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$60,000
Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

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

$719,900
2 Beds ⋅ 2 Baths
Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

121 Merlin Dr, Chester

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$625,000
4 Beds ⋅ 4 Baths
Govern Grason - This home is ready for you to move in. The house has been freshly painted inside and outside; you will appreciate the hardwood floor throughout. The home features 4 bedrooms 3.5 baths and additional space for home office and Walkin storage area that would be finished for more living space if needed. Partial basement, as well as a nice garage with new doors and openers. All located on 2.17 acres. This house is a must see!

109 Governors Way, Queenstown

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

$12,500
ABSOLUTE ONLINE REAL ESTATE AUCTION TO THE HIGHEST BIDDER OVER $12,500! Online Bidding Opens - Wednesday, August 12, 2026. Online Bidding Closes - Thursday, August 13, 2026 at 11:00 AM. List price is opening bid only. Two adjoining unimproved residential lots totaling 0.696 acre, more or less, offered as an entirety in the Chesapeake Estates subdivision of Stevensville, Maryland. Situated on Kent Island in Queen Anne’s County, the property is located within an established residential neighborhood with convenient access to area amenities, waterfront recreation and major commuter routes via U.S. Route 50 and the Chesapeake Bay Bridge. Zoned NC-20 (Neighborhood Conservation), the wooded lots front on Maple Road and Bay Drive, both unimproved paper streets. The auction provides an opportunity to acquire residential land in one of Maryland’s most desirable Eastern Shore communities.

Bay Dr, Stevensville

Listing courtesy of A.J. Billig & Company. Contact:

$725,000
5 Beds ⋅ 4 Baths
Nestled on a private peninsula jutting into the tranquil waters of the Wye Mills lake, 132 Denny Lake Road in Wye Mills, MD, is a breathtaking Dutch Colonial gem. Boasting over 3000 square feet of living space, with a fully finished walk-out basement adding a fourth bedroom and two and a half baths in total, this home offers spectacular lake views from every level. Outside, the bulk headed shoreline was completed within the last 30 years, ensuring stability and charm. Perfectly situated for both tranquility and convenience, this home is centrally located—just 15 minutes to Kent Island or Centreville and only a short drive to Easton. Whether commuting to Annapolis (approx. 30 min) or exploring the Eastern Shore, you’ll find every destination within easy reach—making this the ideal blend of serenity and accessibility. A standout feature is the large detached garage with a workshop and a one-bedroom apartment above, complete with a deck overlooking the water—an idyllic retreat. And with its rare Village Commercial zoning, this property is a standout—offering a special mixed-use designation from Queen Anne’s County. It’s ideal for a home-based business, an Airbnb, or other commercial ventures—a truly one-of-a-kind opportunity to live, work, and play in this iconic setting. Cedar roof is about 20 years old w/ a typical life expectance of 40 years. Well and septic were installed in the late 2000's

132 Denny Lake Rd, Wye Mills

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$449,000
3 Beds ⋅ 2 Baths
Immaculately maintained and tucked away on a quiet street, this charming home offers the perfect blend of privacy and convenience with easy access to Route 50—ideal for commuters. Thoughtfully designed as an elevated residence, the home is built above grade to help reduce flood risk while providing a versatile lower level complete with a hobby room and attached garage. The main living level boasts a bright, open-concept floor plan where the kitchen, dining, and living areas flow seamlessly together, creating an inviting space for both everyday living and entertaining. A beautiful sunroom, surrounded by windows, fills the home with abundant natural light and opens to a wraparound balcony, extending the living space outdoors. Also on the main level is a flexible bonus room that can easily serve as a home office, den, studio, or other space to suit your lifestyle. Upstairs, you'll find two spacious bedrooms, a full bath, and a conveniently located laundry area. Large windows throughout the home create a warm, light-filled atmosphere, while the fully fenced yard provides a secure space for pets, play, or outdoor enjoyment. Combining comfort, versatility, and an excellent location, this delightful property is a must-see for buyers seeking a peaceful setting with convenient access to shopping, dining, and major commuter routes.

121 Marshy Creek Rd, Grasonville

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$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. 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 spacious 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 spacious 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. One of the home's standout features is its energy-efficient solar panel system, helping reduce electricity costs while providing long-term savings and sustainability. Additional recent improvements include a new roof with transferable warranty (2023), luxury vinyl plank flooring (2024), new upper-level carpeting (2026), updated kitchen appliances, a vinyl privacy fence (2022), a new garage door (2024), freshly painted interior and paved driveway. 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, 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, and a private setting, 427 Brookfield Drive is a must-see.

427 Brookfield Dr, Centreville

Listing courtesy of Compass. Contact: (410) 429-7425
$549,987
4 Beds ⋅ 3 Baths
Nestled on a peaceful country setting, this well-maintained colonial offers the perfect blend of privacy and comfort. Featuring 4 bedrooms, 2.5 baths, and soaring cathedral ceilings, the home is filled with natural light and spacious living areas. Enjoy cozy evenings by the fireplace or entertain outdoors in your private backyard oasis complete with a saltwater in-ground pool and a large fenced rear yard. The attached 2-car garage and expansive driveway provide plenty of parking. Conveniently located just a short drive from shopping, dining, schools, and major commuter routes, this home offers the tranquility of country living without sacrificing convenience. Electric solar panels to reduce your monthly energy cost. Don’t miss this exceptional opportunity!

611 Clark Corners Rd, Centreville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$299,999
6 Beds ⋅ 2 Baths
Rare opportunity in the highly coveted Love Point community of Stevensville! Nestled on 1.67 acres and bordered by the State of Maryland Department of Natural Resources, this unique property offers a private, peaceful setting surrounded by nature. The existing home is a true blank canvas and presents an incredible opportunity for investors, builders, or buyers with a vision to bring this property back to life. A full renovation is needed, but the possibilities are endless for creating a custom retreat in one of Queen Anne’s County’s most desirable locations. Enjoy the serenity of the natural surroundings while being conveniently located near waterfront destinations, marinas, shopping, dining, and commuter routes. Properties with this combination of acreage, privacy, and location are rarely available. Bring your plans, your imagination, and your vision—this is the perfect project for those looking to create something truly special in Love Point. This is an estate sale being sold strictly as-is.

116 Homestead Ln, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

$699,000
6 Beds ⋅ 5 Baths
***FRESH NEW PRICE!! COME AND EXPERIENCE THIS LUXURIOUS HOME*** Not often do you get a chance to find a LARGE home like this right in the middle of all the AMENITIES Kent Island has to offer: *Waterfront Dining. *Spas. *Resorts. *Shopping. *Water Access. *All this just 2 minutes to the Chesapeake Bay Bridge!! One of the largest models in the sought-after, amenity-rich community of Ellendale + one of the only finished basements on Kent Island, offers you nearly 4,300 square feet, this impressive home features SIX spacious bedrooms, FOUR full bathrooms, and a convenient half bath on the main level. The upper level is designed with privacy in mind, featuring an expansive primary suite with dual walk-in closets and a large en-suite bath with dual vanities and a walk-in shower. A 2nd primary bedroom / Jr. suite and two additional bedrooms connected by a Jack and Jill bath means every upstairs bedroom has direct access to a bathroom. The English basement offers incredible flexibility with 2 additional large bedrooms, a full bath, a spacious family room, and a game room or den area, making it ideal for guests, extended family, or entertaining. The heart of the home is sure to impress as it is an absolutely beautiful kitchen, complete with stainless steel appliances, granite countertops, an oversized island, and a butler's pantry featuring upper and lower cabinetry along with a beverage fridge, creating the perfect coffee or mini bar area. The kitchen opens seamlessly to the family room and casual dining space, while oversized sliding doors lead to a spacious deck overlooking the fenced backyard. At the front of the home, you'll find a private office and a formal dining room, perfect for working from home or hosting family and friends. Ellendale offers fantastic community amenities including a pool, tot lot, walking trails, and creek access for kayaking and other water activities. Conveniently located near shopping, waterfront dining, and just minutes from the Chesapeake Bay Bridge, you'll love everything Kent Island has to offer. Come experience the Kent Island lifestyle in this exceptional home.

247 Breeding Blvd, Stevensville

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

$199,900
3 Beds ⋅ 2 Baths
Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$549,900
4 Beds ⋅ 3 Baths
Professional Photos coming soon. TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

161 Greenwood Creek Rd, Queenstown

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

$70,000
Finally, an affordable building lot! Come check out this mostly wooded 1.22 acres on the edge of the historic town of Church Hill. The owner has a letter from the town saying it should be able to hook into the public sewer. So many fun things to do nearby including theater, marina's, beaches, parks, restaurants and more. Won't last long.

New St, Church Hill

Listing courtesy of Taylor Properties. Contact:

$525,000
2 Beds ⋅ 3 Baths
Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

230 Switchgrass Way Unit #12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$535,000
5 Beds ⋅ 3 Baths
Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester

Listing courtesy of Samson Properties. Contact: 7033788810
$825,000
4 Beds ⋅ 3 Baths
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 Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida 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. Recent improvements include two new (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. 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. 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: 8003833535
$629,900
3 Beds ⋅ 2 Baths
This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$584,999
3 Beds ⋅ 2 Baths
Have you been waiting for your own slice of paradise to come on the market? Well, the wait is over. This home offers over 2,000 sqft of living space. The open concept gives you plenty of space to entertain or areas to have seperate quiet time. Step out back and an inviting pool is waiting for you to dive into. The liner is approx 3 years old so you should have years of worry free enjoyment. This home sits on nearly an acre with mature trees that give you plenty of privacy but with plenty of open space to host large gatherings. There is a great little tiki bar that gives you the feeling of being miles from home and on vacation every day. The community offers 2 waterside areas with great sunrises and sunsets. The Eastern Bay side has the best sunrises around with a picinic area in a park like setting, a place to launch your water toys and a playground for the young ones. The Chesapeake Bay side has a great beach area for launching your (fishing)kayak, paddleboard, etc or just chiil in the sand with your feet in the surf. If you're into fishing this is the spot. Some of the best sunsets you'll ever see. If this sounds like a place you would vacation to once a year just keep in mind this is the Kent Island lifestyle you can enjoy everyday. The epoxy floored garage has an interior entrace to the home to protect you from the elements. The gourmet kitchen has a workspace, an island and a countertop bar area that give guests space to be included in the kitchen activities but out of the way of the cook. There are 3 rooms to hang out in. One is a large sunroom that leads to the backyard with an inviting ingound pool . Another has a gas fireplace and the other has a woodstove that you can cozy up to in the winter months. There is a back up generator that is included just in case. There is an active community clubhouse that offers plenty of things to do. Including but not limited to parades, cook-offs, cook-outs, santa visits, Easter egg hunts, Halloween booths, yoga classes and much more. Volunteers are always appreciated so come and be part of something special. It does the psyche good.... The South Island Trail and Romancoke Pier are just outside the community. Shopping. public schools, multiple waterside resaurants and Bay Bridge access is very convenient. Well, what are you waiting for??? Make your appointment today!!!!!

342 Wicomico Rd, Stevensville

Listing courtesy of Rosendale Realty. Contact: 4107580333
$829,000
They aren’t making any more land so come grab this hard-to-find 14+ acres before its gone. Tucked away from the nearby waterfront communities with its rolling landscape & a private serene pond you will fall in love with this gorgeous property. So much room to play, relax, watch the wildlife and build your dream home. There is future subdivision potential for added value and public sewer is on Chester River Rd. This amazing property fronts on Loblolly Rd and Chester River Rd. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping & recreational activities. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Potential investment opportunity.

Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$399,000
Looking to get away from the hustle & bustle but want to be close to everything in a water oriented setting? Come build your dream home on this beautiful property then relax & watch the eagles, herons and wildlife that frequent the pond on this hard to find lot. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Great investment opportunity.

Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$209,000
Welcome to the water privileged community of Chester River Beach where you will find this water view lot just waiting to have a new home built on it. Enjoy the added bonus of having a large existing garage or stroll down to the beautiful waterfront park and boat ramp. This lot has public sewer access. Embrace the lifestyle you've always wanted on MDs beautiful eastern shore. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Great investment opportunity.

903 Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$329,000
2 Beds ⋅ 1 Baths
Come discover this charming water view cottage nestled in the sought after water privileged Chester River Beach community. This remodeled & inviting home offers the perfect balance of comfort, convenience & lifestyle with plenty of room to add on or up & expand to capture water views. This property is on public sewer. You’ll love spending relaxing mornings or evenings on the front patio or watch the sun set from the waterfront park/boat launch just steps away. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. Check out the virtual tour. All reasonable offers considered & closing help offered with acceptable contract. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Potential investment opportunity.

901 Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$459,000
3 Beds ⋅ 3 Baths
Privacy & serenity you've been searching for on coveted Kent Island in this beautifully maintained ONE-LEVEL rancher, offering over 1,700 square feet of comfortable living on a secluded 0.65-acre homesite. Featuring 3 spacious bedrooms, 2½ baths, an updated kitchen (2025), renovated full bath (2023), Roof (2015), NEW 100' well (2022), this move-in-ready home combines modern updates with everyday convenience. Step outside to your own private retreat with a fenced backyard, sparkling in-ground pool, shady gazebo, and ample room to entertain or simply unwind. A wide concrete driveway provides generous parking, while the rear wheelchair ramp adds accessibility and flexibility. Perfectly positioned just blocks from the Cross Island Trail and Romancoke Pier, with multiple public boat ramps nearby, you'll enjoy the very best of the Kent Island lifestyle. Local shopping, restaurants, waterfront recreation, and an easy commute to both work and play are all just minutes away. Sunporch off kitchen -new windows convey for future install/finishing. Private, updated, and ready for its next lucky owner—this Kent Island gem is one you won't want to miss.

132 Pennick Dr, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$299,000
The Peters Corner Timber property consists of 32 acres of timber. Timber class can be characterized as an old growth stand of oak species with some hickory and other hardwood species mixed in. The property is improved with electric and a camp site area towards the northern boundary line. No perc test on file with the county. Buyer to perform their own due diligence. A portion of the property is encumbered with an Open Space Easement.

Peters Corner Rd, Sudlersville

Listing courtesy of The Land Group. Contact: (410) 934-3478
$749,900
4 Beds ⋅ 3 Baths
Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel appliances, a large center island, and plenty of space to gather with family and friends. The cozy gas fireplace adds warmth and charm to the main living area, while the screened patio is the perfect spot to relax with your morning coffee or unwind at the end of the day.The large primary suite offers a peaceful retreat with a spacious walk-in closet, double vanities, and a walk-in shower. Additional bedrooms AND an office provide plenty of room for guests, hobbies, or just about anything you can think of and the convenient mud room adds extra functionality.Living in Four Seasons at Kent Island means enjoying an incredible lifestyle. Residents have access to a stunning 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and a full-time lifestyle director who keeps the social calendar full of activities including walking clubs, yoga, mahjong, kayaking, pickleball, and more.Kent Island living is all about making new friends, staying active, and enjoying the lifestyle you've worked hard to achieve. Come see why so many people are proud to call Four Seasons home. And if that wasn't enough of a reason to check this out.....the seller will pay the $4000 capital contribution fee with a full price offer!!

233 Peregrine Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333
$619,900
4 Beds ⋅ 3 Baths
Welcome home to this spacious and inviting 4-bedroom, 2.5-bath Colonial located in the sought-after community of Mallard Run, with easy access to the nearby bike trail. With an open floor plan and plenty of room to spread out, this home offers the perfect blend of comfort and convenience. The kitchen is truly the heart of the home, featuring granite countertops, a center island, and new stainless steel appliances, all flowing seamlessly into the main living areas. Just off the kitchen, the large sunroom provides the perfect spot to relax, entertain, or enjoy your morning coffee. Beautiful bamboo flooring adds warmth and character throughout much of the home, while the pellet stove creates a cozy atmosphere during the cooler months. A first-floor laundry room adds everyday convenience. Upstairs, the spacious primary suite offers a walk-in closet and a private bath with double vanities. Three additional bedrooms provide plenty of space for family, guests, or a home office. Step outside to enjoy the composite deck and patio, ideal for summer cookouts and outdoor gatherings. There is even an existing pad for you to bring your hot tub! Additional updates include a roof that's approximately 6 years old and an HVAC system that's approximately 4 years old. If you've been looking for a well-maintained home in a desirable neighborhood with room to live, work, and entertain, this one is not to be missed.

324 Web Foot Ln, Stevensville

Listing courtesy of Rosendale Realty. Contact: 4107580333
$380,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully situated two-story townhome overlooking the tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient location to Route 50 and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and more. Experience the perfect blend of comfort, convenience, and the relaxed Eastern Shore lifestyle. Designed for easy everyday living, the bright, open floor plan seamlessly connects the kitchen, dining area, and living room, where a cozy gas fireplace creates a warm and relaxing space. The adjoining spacious sunroom showcases tranquil pond views, providing the perfect backdrop for morning coffee, quiet evenings, or entertaining guests. The main level also features a desirable first-floor primary suite with a walk-in closet, private access to the sunroom, and an en-suite bath complete with a relaxing Jacuzzi tub and separate walk-in shower. A flexible bonus room with a laundry area and French door access offers endless possibilities as a home office, den, additional bedroom, craft room, or fitness space. Upstairs, two generously sized bedrooms and a full bath provide comfortable accommodations for family and visitors. As an added bonus, a brand-new roof is currently being installed by the HOA, offering peace of mind and added value for the new owner. Whether you're looking for a full-time residence, a weekend getaway, or a low-maintenance retreat, this exceptional pond front home offers the very best of Kent Island living. Don't miss this rare opportunity—it's more than a home, it's a lifestyle!

6010 Bridgepointe Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333
$899,000
3 Beds ⋅ 3 Baths
Escape to your own private Eastern Shore sanctuary! Nestled on 15.39 acres in Stevensville, 225 Batts Neck Road offers the ultimate blend of coastal convenience and secluded mountain-getaway. This stunning 3BR/2.5BA post-and-beam cabin welcomes you with a classic wrap-around porch and a cozy interior featuring a wood-burning stove—complete with a second fireplace rough-in for the upstairs lofted primary suite. The expansive layout includes an amazing living room and game area designed for hosting memorable family gatherings. The 15+ acres are an outdoor enthusiast's dream, featuring established walking and ATV trails, along with cleared open areas perfect for camping and firepits. Whether you are looking for a premier hunting retreat, a weekend getaway, or a permanent homestead with the potential to build a second home, this unique acreage delivers. Enjoy the best of the Eastern Shore: less than 2 miles from Matapeake Beach, 2.5 miles from Kentmorr Marina, and 4 miles from Bay Bridge Marina. Best of all, you are just 4 miles from the Bay Bridge for a seamless commute to Annapolis, Baltimore, or DC!

225 Batts Neck Rd, Stevensville

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442
$2,840,000
3 Beds ⋅ 2 Baths
Rare Find - 2 houses on one waterfront property! Each with unobstructed views of the water! Privacy without isolation. This will change your mind if you think you need 5 acres or more to have wide open spaces and not have neighbors breathing down your neck! Discover a captivating blend of traditional charm in the vintage cape cod - the main 3-bedroom, 2-bathroom residence, recently updated in spring 2026. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors and upgraded countertops that elevate the kitchen, a home perfect for gatherings. The cozy living room, complete with a brick fireplace and mantel, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom and a traditional floor plan that flows seamlessly throughout. The exterior is equally impressive, featuring a private beach and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. Additional highlights include a guest house(2BR, 1.5 BA, KT,screened porch) and a storage building providing versatility for equipment or hobbies. The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or garden. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

$490,000
2 Beds ⋅ 3 Baths
Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright, open floor plan, gorgeous luxury vinyl plank flooring, and the seamless flow between the kitchen, dining, and living spaces—ideal for entertaining while still offering comfortable, defined living areas. The gourmet kitchen opens effortlessly into the main living space, while the dedicated home office features custom built-in cabinetry, display shelving, and accent lighting, creating an inviting workspace or library. Throughout the home you'll find quality upgrades including plantation shutters in both bedrooms, custom closet organization systems, ceiling fans, and a built-in wireless audio system with a Samsung Frame TV, blending everyday comfort with modern convenience. The spacious primary suite offers a relaxing escape, while the thoughtfully designed split-bedroom layout provides privacy for overnight guests. One of this home's most captivating features is the private balcony overlooking protected wooded surroundings, where you'll enjoy peaceful mornings with coffee while watching deer, birds, and the abundant wildlife that make Kent Island so special. Just outside your door, enjoy convenient access to the Cross Island Trail, nearby Macum Creek, and community kayak storage—perfect for embracing the Eastern Shore lifestyle. Residents of Four Seasons at Kent Island enjoy a truly carefree lifestyle with exterior maintenance, landscaping, and common areas maintained by the HOA, making it easy to lock the door and travel without worry. Resort-style amenities include a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, walking trails, and an active calendar of clubs and social events. Beautifully upgraded, impeccably maintained, and ideally situated, this former model home offers a rare opportunity to enjoy resort-style living surrounded by the natural beauty of Kent Island.

1000 Herons Nest Way Unit #23, Chester

Listing courtesy of Samson Properties. Contact: 7033788810