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21338 Virginia Ave, Chestertown
$400,000
2 Beds ⋅ 2 Baths
Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms , and two fully appointed bathrooms, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

4072 Main St, Trappe
$349,900
3 Beds ⋅ 2 Baths
Totally updated within the past year. Move-in ready, this one-level home offers 3 bedrooms and 2 full baths with LVP flooring throughout most of the home, Appliances replaced in kitchen, freshly painted, separate dining area, and a spacious living room. The primary bedroom includes a private bath. Major 2025 -2026 improvements include a HVAC system with all ductwork replaced in 2026. Return vents in every room. An encapsulated crawl space, new roof 2025 with warranty, new siding, new windows, new doors and new hardware. Fluharty electric replaced all outlets, and switches. Plumbing updated with new shut off valves in utility area. Comfort height toilets added in renovated bathrooms. Outside, you'll find a storage shed and a gravel driveway with ample parking. Conveniently located near downtown Trappe with fabulous dining options and two parks. See list of improvements. Close to public boat ramp. This home is ideally situated between Easton and Cambridge. A well-maintained, updated home offering excellent value and easy living on Maryland's Eastern Shore.

4072 Main St, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Oregon Road, Stevensville
$674,900
4 Beds ⋅ 3 Baths
Beautifully appointed Modern Farmhouse! Massive kitchen with quartz countertops, farm-style sink, stainless appliances, huge island with plenty of seating as well as additional dining space. Open Family Room, Dining Area, and Kitchen layout. Separate living space on the 2nd floor for a more private hang out area or home office. Powder room is tucked away from the main living area on the first floor for privacy as is the separate laundry room. LVP flooring runs throughout the entire first floor. Master suite has broad waterviews of Prices Creek and even the Chesapeake Bay. Sit on the back porch, enjoy your coffee, and enjoy the transquility. Some of the best sunsets you'll ever see can be had from a short walk from your front door. Or walk down to the water's edge and cast your line into the bay as the sun sets. Time to pick colors, customize finishes, and put your own touches on this new home! Photos may show options.

Oregon Road, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

28910 Jennings Rd, Easton
$2,495,000
4 Beds ⋅ 4 Baths
Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

28910 Jennings Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

32301 Main St, Queen Anne
$425,000
3 Beds ⋅ 3 Baths
Step into a piece of Eastern Shore history with this charming, beautifully maintained American Four Square, where original craftsmanship and timeless character create a home that feels truly special. Original doors, staircase, picture windows, plaster and lath walls, beautiful trim and floors, classic built-ins, and a welcoming wraparound porch evoke a simpler pace of life. Adding to the property's unique story is the retired U.S. Post Office building, a remarkable historic feature that gives this property a sense of place and a connection to the town’s rich history. With its own parking, the Post Office offers an excellent opportunity for an on-site professional office or cottage industry. Inside the house, 3 bedrooms and 2.5 baths are complemented by a country kitchen with newer appliances, downstairs laundry, parlor, living room, and formal dining room with built-in cabinetry. Upstairs, the original bath has been renovated and features an antique mahogany vanity matched with the original tub, to which a shower has been added. A second spacious bath has been renovated and features an antique walnut vanity with marble countertop and a step-in shower. A new heat pump upstairs and a split unit downstairs were added in 2023. The water heater was replaced this summer. There is a screened rear porch off the kitchen that backs to woods and a fenced yard. The entire property is complemented by mature landscaping, including many natives, a small water feature, plus pawpaw, persimmon, and fig trees, making it the perfect setting for entertaining, birdwatching. Programmable landscape lighting shows off the property each evening. Additionally, the cellar, attic, storage shed with lofts, and detached garage with workbench and loft add versatility and plenty of storage. Conveniently located on Alt. Rt. 404 near Rt. 309, the property offers quick access to the boat ramp at Hillsboro, Adkins Arboretum, Frederick Douglass Park, and nearby Tuckahoe State Park. Annapolis is only 45 minutes away, and BWI Airport is approximately 75 minutes away. More than a home, this is a rare opportunity to own a distinctive century property and make it part of your own story.

32301 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact:

305 Roe Ingleside Rd, Centreville
$998,500
3 Beds ⋅ 3 Baths
A rare opportunity to enjoy the freedom of country living without sacrificing convenience! Set on 17 diverse acres, this distinctive property offers an exceptional combination of privacy, versatility, and charm. Whether you envision horses grazing in the pasture, a small hobby farm, peaceful afternoons exploring your own land, or simply room to spread out and enjoy the outdoors, this property offers endless possibilities. Tucked into its picturesque setting, the custom-built home welcomes you with a classic covered front porch overlooking the expansive front lawn. Inside, thoughtful design meets comfortable everyday living. The inviting living room features soaring vaulted ceilings, true hardwood floors, and a beautiful stone fireplace that serves as the heart of the home. An open dining area flows into the spacious eat-in kitchen, complete with a center island and tile flooring. The first-floor primary suite offers the ease of main-level living, while the home's flexible layout provides 3–4 bedrooms and 2.5 baths. Outdoor living is equally inviting, with generous composite decking and a screened porch perfect for enjoying the peaceful surroundings. A two-car garage with finished space above adds even more flexibility. What truly sets this property apart is its versatility beyond the main residence. An additional building features a functional office, loading dock, and spacious covered shed, offering exciting possibilities for a home-based business, hobbies, equipment storage, or other pursuits. Enjoy the best of both worlds with a private country setting and convenient access to Centreville, tax-free shopping in Middletown and Dover, and the Bay Bridge. Properties offering this much land, flexibility, and opportunity are increasingly hard to find. Come discover a place where your vision has room to grow!

305 Roe Ingleside Rd, Centreville

Listing courtesy of Select Land & Homes, LLC. Contact:

100 Wall St, Queenstown
$399,900
Situated on a prominent corner lot in downtown Queenstown, this three-level Victorian property, built in 1856, offers a variety of possibilities for residential or commercial use. Zoned CR (Commercial Residential), the property presents potential for a bed-and-breakfast, boutique retail shop, hair salon, professional offices, or other business ventures. Featuring six bedrooms/office spaces, two full bathrooms, and original architectural details, the building offers considerable flexibility for future use. The generous lot provides potential for additional off-street parking to accommodate customers or guests. Located just minutes from Route 50 and the Queenstown Premium Outlets, the property benefits from proximity to a major travel corridor and the area’s shopping destinations. An opportunity to establish a business in historic Queenstown with room to bring your vision to life.

100 Wall St, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

100 Wall St, Queenstown
$399,900
6 Beds ⋅ 2 Baths
This exquisite Colonial home, beautifully renovated in 2010, seamlessly blends historic charm with modern luxury. Spanning 1,840 sq. ft. , the interior boasts six spacious bedrooms and two full baths, featuring elegant wood and carpet flooring throughout. The heart of the home is the inviting country kitchen, equipped with stainless steel appliances, perfect for culinary enthusiasts. Enjoy cozy evenings by one of the two gas fireplaces, or host gatherings in the formal dining room. Set on a generous 0.2-acre corner lot, this property offers a cleared outdoor space ideal for relaxation or entertaining. Just blocks away, indulge in the serene beauty of Queenstown Harbor, where water activities like boating, fishing, and swimming await. With convenient off-street parking and a gravel driveway, this home provides both comfort and accessibility. Experience a lifestyle of tranquility and elegance in this remarkable residence, where every detail invites you to unwind and create lasting memories.

100 Wall St, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

622 Spaniard Neck Rd, Centreville
$729,900
4 Beds ⋅ 3 Baths
**SELLER OFFERING $10,000 TOWARD BUYER'S INTEREST RATE BUYDOWN OR CLOSING COSTS!** More purchasing power. More possibilities. And nearly five acres to make them your own. This isn't just a home with acreage—it's the opportunity to live a little differently. Set on 4.74 private acres just outside of Centreville, 622 Spaniard Neck Road pairs country living with the space, infrastructure, and flexibility to create the lifestyle you've been looking for. A gated driveway adds another layer of privacy as you enter the property. AG certified and already equipped with a 24' x 30' pole barn featuring 10' ceilings, power and water, an additional 11' x 30' lean-to, and a separate run-in, the property is ready for horses, livestock, equipment, hobbies, a serious workshop—or simply room to spread out. Inside, the 4-bedroom home offers a layout that is anything but ordinary. The main living level was designed to take advantage of the surrounding property, with elevated living spaces, expansive views, and multiple access points to the outdoor decks. A dramatic two-story family room anchors the home, while the completely renovated kitchen brings a fresh, modern feel to the heart of the house with refinished cabinetry, quartz countertops, backsplash, stainless steel appliances, open shelving, and a dedicated coffee bar. New LVP flooring throughout the main living areas further refreshes the space, with new carpeting upstairs completing the updates. The spacious primary suite is tucked away upstairs with a private bath and its own cozy, private deck—the perfect spot for morning coffee, watching the wildlife, or winding down as the sun sets over the property. A catwalk overlooking the great room adds architectural character you won't find in a cookie-cutter floor plan. Additional bedrooms provide flexibility for family, guests, or home office space. The lower level adds another layer of possibility with garage-style space designed for ATV, lawn equipment, and recreational storage rather than conventional vehicle parking, along with multiple framed areas ready to be finished around your needs. Outside, mature trees and established grounds create a peaceful, park-like setting with plenty of room to garden, entertain, keep animals, or simply enjoy the privacy. Multiple decks extend the living space outdoors, while mature fruit-producing cherry trees add to the property's established country setting. Nearly five acres. AG certified. Gated privacy. A powered and plumbed pole barn. Room for animals, equipment, and big ideas. **And now, with $10,000 in seller assistance available toward an eligible interest rate buydown or closing costs, the opportunity gets even better!** Seller assistance is subject to lender approval and applicable loan guidelines. 622 Spaniard Neck Road isn't about having more house. It's about having more possibilities.

622 Spaniard Neck Rd, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

108 Gloucester Rd, Queenstown
$574,900
3 Beds ⋅ 3 Baths
Desirably located in Queen Anne Woods just off Bennett Point Road, this impressive brick-front colonial offers a rare combination of privacy, space, and convenience. Significant updates include a brand-new roof (2026), HVAC replacement (2021), new distribution box for septic system (2026), reverse osmosis system installed (2026), updated kitchen and bathrooms, updated windows, doors and siding, fresh interior paint, modern light fixtures, and a Trex deck. Set on a beautiful 1-acre wooded homesite, the home blends timeless appeal with extensive updates and exceptional pride of ownership. Meticulously maintained and move-in ready, it offers a wonderful balance of comfort and flexibility, with no homeowners association and room to enjoy the property on your own terms. Inside, gleaming hardwood floors, fresh interior paint, modern light fixtures, and beautiful interior wood shutters throughout create a warm and refined atmosphere. The welcoming foyer opens to a formal living room or den and a separate dining room, providing inviting spaces for entertaining and everyday living. At the heart of the home, the updated kitchen features granite countertops, counter seating, and brand-new stainless steel appliances, complemented by an adjoining breakfast area and comfortable family room. Glass doors open to the new Trex deck, extending the living space outdoors and overlooking the peaceful, wooded backyard. A main-level powder room and convenient laundry and mudroom with storage connect to the two-car side-entry garage. Upstairs, the spacious primary suite features a generous walk-in closet and a beautifully remodeled en-suite bath with a glass-enclosed tiled shower and built-in seat. Two additional bedrooms and office/bonus room offer flexibility for family, guests, or a home office. A beautifully remodeled hall bathroom with a tub and shower combination completes the upper level. Outside, a spacious and flat backyard that is surrounded by mature trees creates a private, natural backdrop to enjoy throughout the seasons. The Trex deck is ideal for outdoor dining and relaxation, while a storage shed with built-in shelving provides additional storage. The expansive paved driveway offers ample parking, including additional space for your boat. With its extensive updates, meticulous upkeep, generous acreage, and freedom from HOA restrictions, this Queen Anne Woods colonial offers the opportunity to settle in and enjoy the best of comfortable Eastern Shore living. Conveniently located off Bennett Point Road, with easy access to Route 50 and nearby boat ramps, this property combines a peaceful setting with everyday convenience.

108 Gloucester Rd, Queenstown

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

1606 Marion Quimby Dr, Stevensville
$285,000
3 Beds ⋅ 2 Baths
Welcome to 1606 Marion Quimby Drive in Stevensville, Maryland! Enjoy convenient, low-maintenance living in this inviting upper-level condo offering 3 bedrooms, 2 full baths, and 949 square feet of comfortable living space. Step inside to discover a functional floor plan featuring a cozy wood-burning fireplace, perfect for relaxing evenings at home. The private balcony provides a wonderful spot to enjoy your morning coffee or unwind at the end of the day. Additional conveniences include in-unit laundry, making everyday living that much easier. Beyond the condo itself, residents can enjoy the added benefits of a community designed for convenience and relaxation. Spend warm summer days lounging by the community’s in-ground swimming pool, take advantage of the recreation center, and enjoy the beautifully landscaped, professionally maintained common areas. With exterior common-area maintenance handled for you, there’s more time to enjoy everything Kent Island has to offer. It’s a wonderful combination of affordable comfortable living, community amenities, and everyday convenience! Location is everything! Conveniently situated near grocery stores, shopping, restaurants, and everyday essentials, with quick access to Route 50 and the Chesapeake Bay Bridge. Commuters will appreciate the easy drive to Annapolis and surrounding areas while enjoying all that Kent Island has to offer. Even better, the seller is offering a $5,000 contribution toward buyer closing costs or an interest rate buy-down, subject to lender approval and applicable loan guidelines! This added incentive provides an opportunity to help reduce upfront expenses or potentially lower monthly mortgage payments. Whether you’re purchasing your first home, looking to downsize, or searching for an Eastern Shore getaway, this property offers a wonderful combination of comfort, convenience, and location. Schedule your private showing and discover the possibilities!

1606 Marion Quimby Dr, Stevensville

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

105 Placeks Ln Ln, Stevensville
$777,900
4 Beds ⋅ 3 Baths
The Windermere combines all of the home design elements our purchasers love the most. On the main level you’ll love the open plan design with a huge kitchen with a9 foot island,breakfast/sunroom and family room! Formal living room/office and dining room, and two-story foyer complete the space. Upstairs 4 spacious bedrooms include an owner’s suite with spacious walk-in closet or choose the optional super bath and get two walk-in closets! A lower level offers numerous options for expanding your living space to suit your lifestyle. Placek Place is 1 minute to the brige. It offers The Eastern shore Way of Life. Close to pickle ball courts, walking trails, beaches and golf course. Shopping and restaurants too. Western shore features like publicwater, sewer ,sidewalks and full basements. Easy to see why it is 60% sold out.

105 Placeks Ln Ln, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

21905 Harrington Park Rd, Rock Hall
$650,000
4 Beds ⋅ 2 Baths
Welcome to this lovely Cape Cod-style, four-bedroom, two-full-bath home situated on .98 acre in Rock Hall, where comfortable living, peaceful surroundings, and the relaxed charm of Maryland Eastern Shore come together. A welcoming front porch invites you inside to a spacious living room featuring carpet and floating flooring, an open ceiling accented by beautiful exposed wood beams, two ceiling fans, and a distinctive two-sided fireplace that brings warmth and character to the space. The kitchen features stainless steel appliances, a pantry, and plenty of room for everyday living and entertaining. The upper level features a spacious primary bedroom with carpet and a ceiling fan, along with a private primary bath complete with a relaxing Jacuzzi tub and separate shower. The second bedroom offers carpet, a ceiling fan, a walk-in closet, and a skylight that fills the room with natural light. Just outside, the Trex deck provides a peaceful place to relax and take in beautiful views of the pool, private backyard, and surrounding farmland. On the main level, the front bedroom features carpet and a ceiling fan and is conveniently located near the full bath, complete with corian and tile finishes, a handicap-accessible walk-in shower, and a storage cubby. The rear bedroom, also featuring carpet and a ceiling fan, provides direct access to the screened-in back porch. With Trex flooring, two ceiling fans, and peaceful views of the pool and surrounding farmland, the porch is an inviting spot to enjoy your morning coffee, relax at the end of the day, or simply appreciate the quiet surroundings. Step outside and discover your own private backyard retreat. The vinyl-lined pool is surrounded by a river-stone patio and beautiful mature landscaping, including Japanese maples and crepe myrtles. Wood and wrought-iron fencing add privacy and character, with a pool shed and an additional shed for lawn equipment provide convenient outdoor storage. For those who enjoy life on the water, this location offers wonderful access to everything the Rock Hall area is known for. Grays Inn Creek Marina is approximately two minutes away, with access to Grays Inn Creek and Harrington Creek, which flow into the Chester River. A public landing and pier are also nearby, making it easy to enjoy some of the Eastern Shore’s favorite pastimes—fishing, crabbing, sailing, and boating. Approximately 2.6 miles to downtown Rock Hall welcomes you with restaurants, quaint shops, marinas, and all the unique character of life along the Chesapeake Bay. Whether relaxing by the pool, taking in the peaceful country views, or spending the day on the water, this home offers a wonderful opportunity to enjoy the natural beauty, coastal charm, and laid-back lifestyle that make Rock Hall and Maryland’s Eastern Shore such a special place to call home.

21905 Harrington Park Rd, Rock Hall

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

8362 Colony Cir, Easton
$465,000
4 Beds ⋅ 3 Baths
One of the best lots in Matthewstown Run! This 4 bedroom, 2.5 bath home backs up to a farm field with peaceful open views and no neighbors behind you. It has a country, secluded feel and is still close to everything Easton has to offer. The open living room and kitchen share a wood-burning fireplace, perfect for chilly nights. The primary suite has a soaking tub and a large walk-in closet. The 10x20 back porch was enclosed and conditioned with a mini-split, beautiful hickory floors, a closet and privacy doors, so it works as an office, playroom, or bonus room. Outside, the fenced backyard and hardscape patio are made for entertaining, and there’s an attached 2-car garage. Recent updates include a new tankless water heater, new stove, and 5 new upstairs windows. Schedule your showing today, this house will go quickly!

8362 Colony Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

414 Narnia Dr N, Grasonville
$764,500
4 Beds ⋅ 4 Baths
Custom Home with In-Ground Salt Water Pool, Private Backyard & Detached, Heated and Cooled Studio/Office in Greenwood Community. Discover the distinctive charm of this custom-built home in the sought-after Greenwood Community of Grasonville. Providing four bedrooms, and three-and-a-half- bathrooms, this home combines thoughtful craftsmanship, architectural character, and inviting indoor-outdoor living. Step inside to a light-filled, open layout highlighted by a dramatic two-story family room, soaring ceilings, expansive windows, and an impressive stone fireplace. Hardwood floors, crown molding, decorative leaded-glass windows, rounded wall corners, and distinctive lighting add character throughout. The spacious kitchen features granite counter tops, a generous center island, under-cabinet lighting, and stainless steel appliances, including a double-oven range and beverage cooler. The adjoining dining room overlooks the backyard, creating a welcoming setting for everyday meals and entertaining. A main-level bedroom with a full bathroom offers added flexibility for guests or multi generational living. Upstairs, the spacious primary suite provides a relaxing retreat with a tray ceiling, expansive walk-in closet, and private bath featuring a glass-enclosed shower and jetted soaking tub. Two additional bedrooms and a custom-designed second-floor laundry room with extra storage complete the upper level. The outdoor setting is a standout feature, with an in-ground salt water swimming pool, deck, and backyard designed for relaxing, entertaining. A charming, cottage-inspired studio/office with heating and cooling provides versatile space for hobbies, creative pursuits, a home office, or a personal retreat. Residents of Greenwood Community enjoy amenities including a playground, pavilion, large multipurpose field, designated storage for RVs, boats, and trailers, and a gazebo for community gatherings.

414 Narnia Dr N, Grasonville

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

105 Oakmont Ave, Church Hill
$599,999
4 Beds ⋅ 3 Baths
Welcome to 105 Oakmont Road, a truly grand residence on the finest lot in the neighborhood. Built in 2024 and finished with every upgrade the builder offered, this stunning 4 bedroom, 3 bath home delivers 3,144 square feet of elegant, move-in ready living without the wait or the compromises of new construction. From the moment you arrive, the setting sets this home apart, with sweeping views across the street to the community pond creating a peaceful, picturesque backdrop you will enjoy every single day. Step inside and you will find a home that is as beautiful as it is impressive, with spacious, light-filled living areas designed for both everyday comfort and memorable entertaining. Every room reflects the care and quality of a fully upgraded build, from the gathering spaces to the generously sized bedrooms and beautifully appointed baths. Picture slow mornings with coffee overlooking the water, evenings watching the sunset settle over the pond, and plenty of room to host friends and family in style. Stunning from top to bottom and inside and out, this is the rare opportunity to own a nearly new, fully upgraded home in an unbeatable location in Church Hill. Homes like this, on a lot like this, do not come along often. Schedule your private showing today and experience 105 Oakmont Road for yourself.

105 Oakmont Ave, Church Hill

Listing courtesy of Realty Plus Associates. Contact:

21380 Fairbank Circle Cir, Tilghman
$595,000
3 Beds ⋅ 2 Baths
BE SURE TO WATCH THE VIDEO TOUR TO EXPERIENCE THE PROPERTY AND SETTING. Rare opportunity in the coveted Village of Fairbank on Tilghman Island. Set on nearly an acre in a peaceful Eastern Shore setting, this charming 1900 traditional home offers 1,720 square feet of living space with three bedrooms, two full baths, and the warmth and character of a wood-burning fireplace. One of the property's most distinctive features is its setting along Black Walnut Cove, just beyond the backyard, offering an idyllic backdrop for kayaking, canoeing, and enjoying life near the water. The expansive .93-acre lot provides plenty of room for outdoor entertaining, gardening, or simply relaxing and taking in the natural surroundings. Fairbank on Tilghman is a special community where neighbors know one another and take care of eachother. Whether you're searching for a full-time residence or a weekend retreat, this property offers a wonderful opportunity to enjoy the character of Tilghman Island, the beauty of the Chesapeake Bay region, and a lifestyle centered around the water. Just minutes from the restaurants, marinas, and charm of Tilghman Island, 23180 Fairbank Circle is an opportunity to make this unique Eastern Shore community your own. Located 20 minutes from St. Michaels!

21380 Fairbank Circle Cir, Tilghman

Listing courtesy of Compass. Contact:

21560 Spinnaker Way, Tilghman
$699,900
Discover an extraordinary opportunity to embrace a luxurious lifestyle on this stunning 4.05-acre waterfront property, nestled along the serene banks of Harris Creek  With an impressive 295 feet of water frontage. Located in Tilghman on Chesapeake where you will enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available, that you can use while you build your own pier, as this lot offers an approved private dock site, one of only 4 in the community. The natural beauty surrounding this property provides the backdrop for any dream home with the potential for a pool, landscaping or luxurious outdoor living spaces. This exceptional property is not just a piece of land; it's a canvas for your vision of a perfect lifestyle, where the beauty of nature meets the comforts of home as you share your world with the daily visits of eagles, herons and deer. The private drive bordered by protected land is used to access just a hand full of lots and gives you a great sense of privacy.

21560 Spinnaker Way, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

13579 Rustling Oaks Dr, Wye Mills
$749,000
4 Beds ⋅ 4 Baths
13579 Rustling Oaks Drive offers four bedrooms, three full bathrooms, and one half bathroom in the desirable Preserve at Wye Mills. Set on a beautifully landscaped three-quarter-acre lot, this light-filled home features an owner's suite on the main level and a convenient location between Easton and Annapolis. The gourmet eat-in kitchen is appointed with granite countertops, hardwood floors, cherrywood cabinetry, double sinks, a refrigerator, dishwasher, microwave, double oven, and a center island with a five-burner induction cooktop. Direct access leads to the garden deck, making indoor-outdoor entertaining effortless. Off the kitchen, the 13-by-14-foot formal dining room features hardwood floors, crown molding, chair railing, and two windows. A 10-by-13-foot flex room also offers hardwood floors, crown molding, and two windows. The impressive 20-by-17-foot living room has cathedral ceilings, a propane fireplace, carpeting, and ceiling fans. A 12-by-10-foot office with double doors, hardwood flooring, a ceiling fan, and a window provides a comfortable private workspace. The 16-by-18-foot main-level owner's suite includes carpeting, ceiling fans, four windows, and a spacious walk-in closet. Its private bathroom features dual sinks, tile flooring, a soaking tub, and a glass-enclosed walk-in shower. Upstairs are three carpeted bedrooms and two full bathrooms. Bedroom 2 measures 14 by 13 feet and includes a private bathroom. Bedrooms 3 and 4 share a Jack-and-Jill bathroom with dual sinks, tile flooring, and a tub-shower combination. Bedroom 3 measures 13 by 13 feet, while Bedroom 4 measures 13 by 14 feet and includes a ceiling fan. Additional highlights include a full basement with walkout stairs and an 8-by-11-foot wine cellar. The property provides easy access to BWI Airport, Washington, D.C., and Maryland's beaches.

13579 Rustling Oaks Dr, Wye Mills

Listing courtesy of Benson & Mangold, LLC. Contact:

29752 Gabler Ct, Easton
$499,000
3 Beds ⋅ 2 Baths
Discover refined one‑story living enhanced by a full, pristine, ready‑to‑customize basement in this beautifully maintained three‑bedroom residence in Easton. The home’s taupe façade, enriched with stone and blue architectural accents, pairs elegantly with vibrant landscaping for standout curb appeal. The main level offers a thoughtfully designed layout: three bedrooms, two full baths, a gracious family room with gas fireplace, formal dining room, sunlit breakfast area, and a chef’s kitchen appointed with granite surfaces and extensive cabinetry. A well‑placed laundry/mudroom adds convenience. Downstairs, the impressive 2,224‑square‑foot basement provides exceptional potential—cool year‑round and easily adaptable for additional living space, including a bedroom with egress, recreation areas, or specialty rooms. Exterior highlights include a two‑car garage, paved drive, sidewalks, and a fully fenced backyard ideal for privacy and outdoor enjoyment. A large patio off the kitchen/breakfast area creates a perfect setting for entertaining. Hunters Mill also offers a neighborhood park with children’s play equipment. Just five minutes from downtown Easton, this home places you near acclaimed dining, cultural venues such as the Avalon Theatre and Academy Art Museum, boutique and specialty shopping, and nationally recognized festivals including Waterfowl and Plein Air. Saint Michaels and Oxford are just fifteen minutes away, not to mention the 28 public water landings and boat ramps around Talbot County for boating, fishing and waterfront access!

29752 Gabler Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

26546 Presquile Farm Dr, Easton
$7,850,000
7 Beds ⋅ 8 Baths
PRESQUILE MANOR HOUSE – An extraordinary waterfront estate steeped in history, architectural distinction, and timeless elegance. Magnificently positioned along the Wye River with breathtaking panoramic views and coveted western exposure, this distinguished circa-1800 manor house offers an exceptional combination of historic character, refined luxury, and unparalleled waterfront living. Originally part of the historic Lloyd family holdings, the 10.48-acre estate has been meticulously renovated by renowned Peter Zimmerman Architects and West & Callahan Construction, reflecting an extraordinary commitment to preserving its architectural heritage while incorporating the finest modern appointments. The magnificent 7BR/6FB/3HB manor house showcases exquisite craftsmanship throughout, with exceptional millwork, beautifully proportioned rooms, soaring ceilings, rich hardwood floors, elegant fireplaces, and graceful architectural details. Expansive windows fill the interiors with natural light while framing spectacular views of the river and surrounding grounds. A stunning curved staircase with a beautifully crafted wood handrail serves as an architectural centerpiece. Gracious formal living and dining rooms provide elegant spaces for entertaining, while inviting gathering areas offer warmth and comfort for everyday living. The extraordinary gourmet kitchen features extensive custom cabinetry, an expansive center island, premium appliances, and beautifully appointed finishes. Seven generously appointed bedrooms and beautifully renovated baths provide exceptional comfort and privacy for family and guests. Throughout the residence, sophisticated finishes and thoughtful design reflect a remarkable balance between the home's distinguished history and contemporary luxury living. Beyond the residence, the spectacular grounds provide a setting of extraordinary beauty and tranquility. Expansive lawns sweep toward the river, complemented by magnificent mature trees, formal gardens, and beautifully maintained landscaping. A waterside swimming pool offers an idyllic setting for relaxation and outdoor entertaining, while a private tennis court adds to the property's outstanding recreational amenities. Extensive riprapped shoreline and a coveted deepwater boathouse provide exceptional access to the Wye River and surrounding Chesapeake Bay waterways. Sweeping river vistas and magnificent western sunsets create a breathtaking backdrop for this remarkable waterfront retreat. Rarely does a property of such historical significance, architectural refinement, and exceptional waterfront presence become available. Presquile Manor House represents a remarkable opportunity to own one of the Wye River's most distinguished estates, where centuries of history, extraordinary craftsmanship, and the natural beauty of Maryland's Eastern Shore come together in a truly exceptional offering. The estate is approached by an impressive, tree-lined entrance drive extending across approximately 7.1 additional acres, with access secured by a perpetual easement.

26546 Presquile Farm Dr, Easton

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

106 Harlan Loop, Chestertown
$425,000
4 Beds ⋅ 3 Baths
Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

106 Harlan Loop, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

204 Hunters Ridge Rd, Centreville
$749,900
3 Beds ⋅ 3 Baths
You'll love this cottage-style home in the desirable Dulin Clark Road neighborhood of Hunter's Ridge, just a few miles from public parks. This luxurious 3-bedroom, 2 full and 3 half-bath home includes modern amenities such as two sets of washers and dryers, a resort-like backyard complete with a pool and poolhouse with a half bath, Trex decking, and a firepit. A recently added spacious closet system provides abundant storage. The detached garage features a studio apartment with rental potential. A circular paved driveway provides ample, convenient parking and great curb appeal, along with professional landscaping. A shed and easily accessed attic add to the ample storage throughout the home.

204 Hunters Ridge Rd, Centreville

Listing courtesy of Beycome Brokerage Realty LLC. Contact:

212 Baltimore Rd, Stevensville
$625,000
5 Beds ⋅ 3 Baths
Beautifully Renovated Transitional Home in Kent Island Estates! You will fall in love with this stunning transitional home nestled in the desirable waterfront community of Kent Island Estates! Beautifully renovated from top to bottom, this move-in-ready home combines modern style, comfortable living, and thoughtful updates throughout. Step inside to discover gorgeous hardwood flooring, soaring vaulted ceilings, and an inviting open floor plan filled with natural light. The whitewashed fireplace creates a beautiful focal point, while the spacious layout offers incredible flexibility to suit your lifestyle. With space configured for up to five bedrooms, you can easily create the perfect home office, family room, sitting room, hobby space, or guest accommodations. The beautifully updated bathrooms feature stylish tile showers and contemporary floating vanities. Extra-wide sliding glass doors invite the sunshine inside and provide easy access to the wraparound deck, where you can relax, soak up the sun, or fire up the grill for outdoor entertainment. Great new kitchen with stainless and Quartz counters adds even more style to this home. The generous yard offers plenty of room for gardening, games, pets, and all your favorite outdoor activities. A refurbished shed provides convenient storage for tools, lawn equipment, and recreational toys. The home's striking black-and-white exterior is complemented by oversized windows and an upgraded garage door that adds a sophisticated finishing touch. Enjoy peace of mind with major exterior and mechanical updates, including a new roof, siding, windows, deck, and heating system. With convenient one-level living, this home offers the opportunity to enjoy your surroundings comfortably for years to come. Kent Island Estates is a peaceful waterside community close to the fire hall, picnic areas, and playground. You are also approximately seven miles from shopping and convenient access to the Bay Bridge. Stylish, spacious, and move-in ready, this beautifully updated home offers the best of relaxed Eastern Shore living. Come discover all that Kent Island Estates has to offer!

212 Baltimore Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

208 Oakwood Ln, Stevensville
$525,900
3 Beds ⋅ 2 Baths
Charming 3-Bedroom Home with Sunroom Addition, Wood Stove & Detached Garage with Office Welcome home to this inviting 3-bedroom, 2-full-bath home situated on a beautiful 0.33-acre lot, offering a wonderful combination of indoor comfort, outdoor living, and versatile space. Featuring warm wood accents, hardwood floors, a spacious living room, and a cozy wood stove, this home is full of character and possibilities. The living room provides a welcoming gathering space, while the kitchen features abundant cabinetry, stainless steel appliances, generous counter space, and a large island perfect for meal preparation, casual dining, and entertaining. The sunroom addition boasts impressive 12-foot ceilings, creating an open, airy atmosphere with endless potential for a second living area, hobby space, or relaxing retreat. Enjoy the outdoors with both a front porch, screened-in porch, and open porch, offering plenty of options for relaxing, entertaining guests, or enjoying a quiet morning surrounded by nature. The spacious yard, complemented by mature landscaping, provides room for gardening, outdoor activities, and more. The home offers three comfortable bedrooms and two full bathrooms, including a bathroom with a convenient walk-in shower. With inviting living spaces and a thoughtful blend of indoor and outdoor amenities, this property offers comfort, functionality, and room to make it your own. A standout feature is the detached two-car garage with a dedicated office, providing valuable flexibility for working from home, pursuing hobbies, additional storage, or creating a separate workspace. With its charming character, hardwood floors, cozy wood stove, spacious sunroom, and versatile garage, this property presents a wonderful opportunity to enjoy comfortable living with space to spread out. Property Highlights: 3 bedrooms and 2 full bathrooms 0.33-acre lot Hardwood floors Cozy wood stove Sunroom addition with 12-foot ceilings Kitchen with stainless steel appliances and large island Walk-in shower Detached two-car garage with dedicated office Front porch, screened-in porch, and open porch Spacious yard with mature landscaping Come discover the charm, space, and possibilities this home has to offer!

208 Oakwood Ln, Stevensville

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

30603 Dover Rd, Easton
$399,000
2 Beds ⋅ 1 Baths
Scenic farmland views, peaceful country living, and convenient access to Easton and Preston—welcome to 30603 Dover Road. Nestled on two acres in Talbot County, this well-maintained brick rancher offers the perfect balance of privacy, comfort, and convenience. Surrounded by the natural beauty of Maryland’s Eastern Shore, the property enjoys picturesque views of neighboring farmland, expansive lawn, and a tranquil setting just minutes from the everyday conveniences of Easton and Preston. Inside, approximately 2,138 square feet of living space offer a warm and inviting atmosphere. The sun-filled living and dining rooms provide comfortable spaces for relaxing and entertaining, while the generously sized eat-in kitchen serves as the heart of the home. Recently updated flooring throughout much of the main level adds a fresh, welcoming feel. The primary bedroom features a dedicated dressing area, while a second bedroom and full bathroom complete the main-level accommodations. Downstairs, the finished lower level offers exceptional flexibility, with a spacious family room and dedicated home office space. A supplemental propane heater adds comfort during the colder months. Thoughtful recent improvements make this home even more attractive, including a new roof in 2024, replacement windows in 2022 and 2024, new flooring throughout much of the main level, a new water softener and filtration system, and a new reverse osmosis drinking water system in 2026. Outside, the expansive lawn provides endless opportunities for gardening, recreation, entertaining, or simply enjoying the beautiful farmland views. A covered front porch invites slow mornings and peaceful evenings, while the spacious two-car garage provides ample room for vehicles, storage, and workshop projects. Lovingly maintained by just two owners since its construction in 1984, this home is an opportunity to enjoy the space and serenity of country living with the convenience of being a short drive to restaurants, grocery stores, doctors and more. Two acres, scenic Eastern Shore surroundings, and meaningful modern improvements—discover the possibilities at 30603 Dover Road.

30603 Dover Rd, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

114 Pathfinder Cir, Grasonville
$649,000
5 Beds ⋅ 3 Baths
**Welcome to Perry’s Retreat, where spacious living meets modern comfort and Eastern Shore charm!** Built in 2023, this pristine Ryan Homes Lehigh model offers the **largest floor plan in the community**, featuring over 3,000 square feet of beautifully designed living space, five bedrooms, two-and-a-half bathrooms, and an exceptional open-concept layout. The heart of this home is its expansive main living area, thoughtfully designed for both everyday comfort and effortless entertaining. The open floor plan seamlessly connects the kitchen, dining, and gathering spaces, creating a bright and inviting atmosphere. The spacious kitchen features an oversized center island that serves as the perfect gathering spot for casual meals, entertaining guests, or simply enjoying time together. With generous room to spread out, this main level is truly an entertainer’s dream! Adding to the home's versatility is a main-level bedroom, ideal for guests or multigenerational living, along with a separate flex room that can easily accommodate a home office, exercise room, or hobby space. Upstairs, a spacious additional living area provides the perfect secondary retreat for movie nights, a playroom, or a comfortable place to unwind. The generously sized primary suite features two walk-in closets and a private en-suite bathroom. Three additional bedrooms offer plenty of room and flexibility. Step outside to your own private backyard oasis! A beautifully hardscaped patio provides the ideal setting for outdoor dining, grilling, and entertaining. The fully fenced backyard, complete with attractive vinyl fencing and gated access to the expansive community green space, offers a wonderful combination of privacy and convenience. Perry’s Retreat offers a welcoming neighborhood atmosphere with expansive common grounds, a playground, and a dedicated boat storage area for residents. Additional highlights include a two-car attached garage, public water and sewer, and the peace of mind that comes with owning a nearly new home in pristine condition. **With the largest floor plan in Perry’s Retreat, five bedrooms, multiple living areas, an entertainer-friendly open layout, and beautifully finished outdoor space, this exceptional home truly has it all!** Discover the space, flexibility, and lifestyle you've been looking for!

114 Pathfinder Cir, Grasonville

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

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