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5 S Park St S, Easton
$575,000
This stunning Bungalow with a seperate commercial rental was beautifully renovated in 2020 and offers a perfect blend of modern luxury and timeless charm. With 1,168 sq. ft. of meticulously designed space, every corner of this home exudes warmth and sophistication. The open layout invites natural light, highlighting the exquisite craftsmanship throughout. Enjoy the seamless flow between indoor and outdoor living, perfect for entertaining or quiet evenings at home. The property features a versatile office/studio, ideal for remote work or creative pursuits. Nestled on a generous 0.19-acre lot, the lush surroundings provide a serene escape from the hustle and bustle of daily life. Parking is a breeze with ample driveway and street options. This residence is not just a home; it's a lifestyle, offering comfort, elegance, and a sense of community. Experience the joy of living in a space that has been thoughtfully updated to meet the demands of modern living while retaining its unique character. Your dream home and investment awaits!

5 S Park St S, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

301 Oxford Rd, Oxford
$599,000
4 Beds ⋅ 2 Baths
Coming soon! Charming home. Beautiful Community. Coastal Eastern Shore Living! Get ready to fall in love with this inviting 4-bedroom home nestled in the popular Oxford Community! This home offers the perfect blend of traditional charm, comfortable living and wonderful spaces for entertaining family and friends! Ready for your personal touches! This 4 bedroom, 1 1/2 bath has an attached 1 car garage with a relaxing backyard with deck-ideal for morning coffee, outdoor dining or unwinding after a long day. Located along Maryland's beautiful Eastern Shore, Oxford is a picturesque waterfront town known for its rich history, scenic waterways, charming streets and relaxed coastal lifestyle. Enjoy local restaurants, boating, just a few blocks from waterfront views and the small-town atmosphere make Oxford such a special place to call home.

301 Oxford Rd, Oxford

Listing courtesy of Coldwell Banker Realty. Contact:

6209 Sudlersville Rd, Sudlersville
$115,000
3 Beds ⋅ 2 Baths
Opportunity awaits for the buyer with vision and a willingness to roll up their sleeves! Conveniently located in Queen Anne’s County but near the Delaware state line, this property offers a chance to take on a major renovation project and bring new life to a home with plenty of potential. The property also features several storage sheds (some equipped with electricity), offering additional space for storage, hobbies, or projects. The home is in need of extensive repairs and improvements, making it an ideal opportunity for an investor, experienced renovator, or buyer ready to put in the work. With a convenient location and room to explore the possibilities, this could be the project you've been waiting for. Bring your ideas, your tools, and your vision!

6209 Sudlersville Rd, Sudlersville

Listing courtesy of RE/MAX Executive. Contact:

219 Webb Ln, St Michaels
$249,900
2 Beds ⋅ 1 Baths
*Professional photos coming soon! Nestled in the charming downtown of St Michael's, this well-maintained 2 bedroom, 1 bathroom townhouse offers a perfect blend of comfort and convenience. This traditional-style home features an interior with luxury vinyl plank downstairs, cozy carpet flooring upstairs, ceiling fans and a kitchen equipped with modern appliances including a built-in microwave, dishwasher, and electric oven/range, making meal preparation a breeze. Enjoy the convenience of a stacked washer and dryer, along with a tankless instant water heater. Step outside to a cleared rear yard with a privacy fence, perfect for outdoor gatherings. With no thru street, this property offers a peaceful retreat while still being close to the vibrant downtown area. St Michael's is not just a place to live; it's a community that thrives on connection hosting events throughout the year. Residents enjoy the local restaurants, stores, parks, birding trails, boating and waterfront sunsets within walking distance making it an ideal place to call home. Must be owner occupied, no rentals allowed. Schedule your showing today!

219 Webb Ln, St Michaels

Listing courtesy of Coldwell Banker Realty. Contact:

7084 Redwood Ct, Easton
$518,000
5 Beds ⋅ 4 Baths
The Woods at Stoney Ridge - Original owners. Dutchman model in excellent turn-key condition. The owners have meticulously maintained this 3,546+ SF home. It is substantially larger than most in the community. Immediate occupancy. *The tax records do not reflect the finished 3rd floor with a bedroom/fitness/storage room, living/media room, and ensuite bathroom. This is the only home in the community with a finished 3rd floor living space, more square footage. Ideal floor plan for multi-generational living. 5 total bedrooms, 3-1/2 baths, 2 story great room with 17' vaulted ceiling, formal living room, formal dining, office/library (this is one room with mult-usage). Spacious Primary with ensuite bathroom > double vanity, Jacuzzi tub, and water closet. Gas cooking, gas & electric heat, gas fireplace, tankless water heater. Full laundry room off the kitchen. Deck access off the breakfast/kitchen/great room areas. Flooring is a blend of hardwood, tile, and carpet. Bright natural light in all rooms. ACU-RITE Humidity Monitor in the crawlspace with a monitor in the home (see photo). Rear storage shed for lawn equipment. The back area of the lot is wooded, all other areas of the property have mature landscaping. All window treatments, mirror and sconces over the fireplace, and extra garage refrigerator convey. The Woods at Stoney Ridge is conveniently located near the RT 50 corridor, close to schools, medical, shopping, and eateries.

7084 Redwood Ct, Easton

Listing courtesy of Newport Bay Realty. Contact:

28752 Jennings Rd Unit LOT 4, Easton
$650,000
Discover an exceptional opportunity to build your dream home in the sought-after community of Llandaff at Cooke's Hope. Beautifully elevated and overlooking picturesque Peachblossom Creek, this perc-approved waterfront lot offers a peaceful, private setting surrounded by the natural beauty of Maryland's Eastern Shore. Mature trees along the property boundaries enhance the sense of privacy, while scenic creek views and abundant wildlife create a tranquil backdrop. Enjoy opportunities for kayaking, canoeing, and exploring the surrounding waterways. The potential for a private pier offers additional possibilities for enjoying life by the water, subject to buyer verification and applicable HOA approvals. Conveniently located near the charming towns of Easton and Oxford, Llandaff offers a wonderful balance of natural beauty, privacy, and accessibility. The well-established community features common area maintenance and roadside mowing to the split rail fencing, included in the current annual HOA fee of $600. An inviting setting to create a custom waterfront retreat and embrace relaxed Eastern Shore living.

28752 Jennings Rd Unit LOT 4, Easton

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

28776 Jennings Rd Unit LOT 5, Easton
$650,000
Discover an exceptional opportunity to build your dream home in the sought-after community of Llandaff at Cooke's Hope. Beautifully elevated and overlooking picturesque Peachblossom Creek, this perc-approved waterfront lot offers a peaceful, private setting surrounded by the natural beauty of Maryland's Eastern Shore. Mature trees along the property boundaries enhance the sense of privacy, while scenic creek views and abundant wildlife create a tranquil backdrop. Enjoy opportunities for kayaking, canoeing, and exploring the surrounding waterways. The potential for a private pier offers additional possibilities for enjoying life by the water, subject to buyer verification and applicable HOA approvals. Conveniently located near the charming towns of Easton and Oxford, Llandaff offers a wonderful balance of natural beauty, privacy, and accessibility. The well-established community features common area maintenance and roadside mowing to the split rail fencing, included in the current annual HOA fee of $600. An inviting setting to create a custom waterfront retreat and embrace relaxed Eastern Shore living.

28776 Jennings Rd Unit LOT 5, Easton

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

28598 9th Dr, Easton
$995,000
4 Beds ⋅ 5 Baths
Nestled in the Easton Club along the shores of the Tred Avon river, this exquisite Craftsman-style residence offers a harmonious blend of luxury and comfort. Spanning over 3,900 square feet, this home features four spacious bedrooms and 3 full and 2 half bath that are elegantly appointed, including a primary suite with a waterside view, his and her private baths and dressing rooms.. Step inside to discover an inviting open floor plan adorned with rich hardwood floors, ceramic tile, and plush carpeting. The gourmet kitchen is a chef's dream, equipped with stainless steel Wolf gas cooktop and oven, a large island, a butlers pantry, granite counters and an eat in waterside dining nook. Enjoy cozy evenings by the gas fireplace in the living room, enhanced by bookshelves and charming wainscoting. The exterior is equally impressive, featuring extensive hardscaping, lush landscaping, and a private dock site on the Tred Avon River. Embrace outdoor living with a community pool, tennis courts, and a BBQ grill for summer gatherings. The home also boasts an immaculate three-car garage with electric vehicle charging capabilities and ample off-street parking. With water features that include a serene waterfall and a tranquil atmosphere, this home is a sanctuary for those seeking an exclusive lifestyle. Experience the perfect blend of elegance and comfort in this remarkable property.

28598 9th Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

7570 Muirfield Dr, Chestertown
$895,000
4 Beds ⋅ 3 Baths
Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence overlooking the 10th tee and fairway of the Chester River Yacht & Country Club. Set on 1.45 acres of thoughtfully landscaped grounds in the desirable Prestwick community, this exceptional property offers privacy, timeless craftsmanship, and the ease of single-level living. Custom-built by Alton Darling, the approximately 2,500-square-foot home features an inviting, open floor plan with hardwood floors, elegant crown molding, and generously proportioned rooms designed for comfortable everyday living and effortless entertaining. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully appointed bath featuring dual vanities with quartz countertops, an oversized walk-in shower. Two additional bedrooms, thoughtfully situated in a separate wing, offer privacy for family and guests. A formal dining room, breakfast room, and versatile office or 4th bedroom space provide flexibility for today’s lifestyles. The kitchen features granite countertops, updated appliances, and convenient access to the home’s gathering spaces. Freshly painted interiors and numerous system improvements further enhance the property’s appeal. Beyond the interiors, the home’s setting truly distinguishes it. A screened porch overlooks mature landscaping and the picturesque golf course, creating an inviting place to enjoy morning coffee, entertain friends, or simply appreciate the peaceful surroundings. A new hot tub and outdoor gathering area offer additional opportunities for relaxation. An attached two-car garage, generous storage, and extensive mechanical and safety improvements complete this thoughtfully maintained residence. Appliances 2024, washer/dryer 2025 More upgrades in the document section.

7570 Muirfield Dr, Chestertown

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

903 S Washington St, Easton
$525,000
3 Beds ⋅ 2 Baths
Brimming with traditional character, architectural details, and the enduring appeal of solid brick construction, this charming three-bedroom, two-bath rambler offers exceptional one-level living in the sought-after town of Easton, Maryland. Beautifully situated on a generously sized lot along South Washington Street, the home is set well back from the road, surrounded by magnificent trees and mature landscaping. A welcoming brick walkway leads to the front entrance, where the home's delightful character continues throughout its bright, beautifully maintained interior. Gorgeous hardwood flooring, elegant crown molding, custom built-ins, and distinctive architectural details showcase the craftsmanship and timeless appeal of this classic home. Abundant windows fill the spacious living room with natural light, while a traditional wood-burning fireplace and custom built-in shelving create an inviting gathering space. A generously sized formal dining room overlooks the beautiful grounds, and the updated kitchen features granite countertops, stainless steel appliances, a separate pantry, and charming built-in shelving. Just beyond the kitchen, a versatile family room offers additional living or recreation space. Three comfortable bedrooms feature hardwood flooring and attractive recessed lighting, while two full baths include a beautifully renovated bathroom with shiplap accents, a double-sink vanity, LVP flooring, and an expansive tiled walk-in shower. Meticulously maintained, the home benefits from significant recent improvements, including a new roof with 50-year shingles, replacement windows, and gutter guards installed in 2022, along with stainless steel kitchen appliances purchased within the past five years. Outside, the picturesque backyard features magnificent shade trees, and a spacious deck for outdoor entertaining. A charming brick outbuilding with electricity, rear-entry garage, and generous off-street parking add convenience and functionality. Completing this exceptional offering is its premier location in historic Easton, approximately a mile from downtown's acclaimed restaurants, boutiques, art galleries, and cultural attractions. Nearby Idlewild Park, shopping, healthcare, and everyday conveniences further enhance the appeal of this wonderful Eastern Shore setting. Combining timeless architectural charm, thoughtful updates, beautiful grounds, and an outstanding location, this captivating brick home is truly something special. Upcoming Open Houses: Friday 11/13 (2:00-4:00), Saturday 11/14 (10:00-1:00), Sunday 11/15 (10:00-1:00)

903 S Washington St, Easton

Listing courtesy of Northrop Realty. Contact:

818 High St, Chestertown
$3,300,000
Prime Commercial Opportunity in Chestertown!! The Brian E. Bainbridge Health Building is a prominent, three-story commercial property offers 23,000 square feet of versatile space perfectly situated on High Street. Known locally as the home of the premier Aqua Fit Health Center, this highly functional multi-floor building features an excellent mix of large-scale operational facilities and multiple private office suites. The ground level boasts extensive infrastructure, including a custom-built aquatic center with a heated saltwater pool, expansive weight/cardio rooms, and physical therapy areas. The upper floors offer a flexible layout of professional office spaces, ideal for medical practices, wellness professionals, or traditional corporate tenants. Complete with an elevator, high-visibility street presence, and a dedicated customer/tenant parking lot, this unique asset is a turnkey opportunity for an investor or an owner-user looking to establish a major presence in Kent County.

818 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

804 Kimberly Way, Stevensville
$515,000
4 Beds ⋅ 3 Baths
Welcome home! This spacious 4-bedroom, 2.5-bath home offers comfortable living, thoughtful updates, and wonderful outdoor spaces, all situated on a beautiful wooded lot of over half an acre. From the moment you arrive, you'll appreciate the inviting front porch, the perfect spot to enjoy your morning coffee or unwind at the end of the day. Step inside to a welcoming foyer featuring a large walk-in closet and a versatile room to the right that can easily serve as a formal dining room, living room, home office, or whatever best suits your needs. The main level features fresh paint and beautiful new luxury vinyl plank flooring throughout. The updated kitchen is sure to impress with gorgeous new granite countertops, stainless steel appliances, and plenty of workspace. An eat-at countertop provides additional seating and flows seamlessly into a generously sized dining area, making this space ideal for everyday living and entertaining. Just off the kitchen, the family room offers a cozy gathering space with a fireplace (currently non-operational). Enjoy even more living space outdoors with access to a screened-in porch that leads to a spacious wraparound porch overlooking the private, wooded setting. Completing the main level is a convenient half bath with laundry area and access to the two-car garage, which offers built-in shelving for additional storage. Upstairs, you'll find four freshly painted bedrooms, all featuring new carpet and ceiling fans, along with two full bathrooms. The primary suite offers ample closet space and an exciting opportunity to create something special! An exceptionally large unfinished storage room adjoining the primary bedroom provides endless possibilities for a future expanded primary bath, walk-in closet, or additional bedroom living space. Both the primary and hallway bathrooms have been refreshed with new laminate plank flooring. Bedroom two is also a standout with its impressive high ceilings. Beyond the home, enjoy all that this wonderful community has to offer, including a community pool, grills, sports courts, marina, and fishing pier. Conveniently located near downtown Stevensville, you'll love the charming local shops and restaurants, as well as nearby Terrapin Nature Park and the Cross Island Trail. For commuters, easy access to Route 50 and the Chesapeake Bay Bridge makes getting where you need to go a breeze. With its fresh updates, flexible living spaces, generous outdoor areas, and fantastic community amenities, this home offers a wonderful opportunity to enjoy the Eastern Shore lifestyle!

804 Kimberly Way, Stevensville

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

335 Overture Way, Centreville
$545,900
4 Beds ⋅ 3 Baths
SOME HOMES ARE SIMPLY BEAUTIFUL. OTHERS MAKE YOU FEEL AT HOME THE MOMENT YOU WALK THROUGH THE DOOR. WELCOME TO 335 OVERTURE WAY! Nestled within the highly desirable 55+ community of Symphony Village, this exceptionally beautiful home offers the perfect blend of timeless elegance, sophisticated style, and inviting warmth! From the moment you enter, you’ll appreciate the gorgeous flooring, rich designer-inspired colors, elegant architectural details, and beautiful plantation shutters throughout. The stunning formal dining room, with its dramatic navy walls and exquisite chandelier, creates a wonderful setting for memorable gatherings. The gorgeous kitchen is truly the heart of the home, featuring crisp white upper cabinetry, rich blue lower cabinetry, gleaming countertops, stainless steel appliances, and a beautiful tile backsplash. Opening to the inviting family room with its cozy fireplace and abundance of natural light, this space is perfect for both everyday living and entertaining. The spacious main-level primary suite offers a peaceful retreat with TWO walk-in closets and a beautifully appointed private bathroom featuring a soaking tub, separate walk-in shower, and double sinks. A second main-level bedroom provides wonderful flexibility for guests or a home office. AND THERE’S SO MUCH MORE! The expansive, beautifully finished WALKOUT lower level offers two additional bedrooms, a full bathroom, and a generously sized second family room, providing incredible flexibility for entertaining, overnight guests, hobbies, or simply relaxing. Abundant storage adds even more convenience to this thoughtfully designed home. Step outside onto the lovely deck overlooking a peaceful wooded setting, where you can enjoy your morning coffee, unwind after a long day, or simply watch the deer wander through the trees. It’s the perfect place to appreciate nature and the beauty of every season. Beyond your doorstep, Symphony Village offers an exceptional 55+ lifestyle with resort-style amenities, including a clubhouse, indoor and outdoor swimming pools, fitness facilities, and a wonderful variety of recreational and social activities. BEAUTIFULLY APPOINTED, THOUGHTFULLY DESIGNED, AND SURROUNDED BY NATURAL BEAUTY — 335 OVERTURE WAY IS MORE THAN JUST A HOUSE. IT’S A WONDERFUL PLACE TO CALL HOME!

335 Overture Way, Centreville

Listing courtesy of Chaney Homes, LLC. Contact:

4020 Eastern Neck Rd, Rock Hall
$799,000
4 Beds ⋅ 2 Baths
This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at the rear of the property could remain in ag use as tilled land and/or be used for hunting or as a horse farm. With ample room to customize, this home is a canvas for your personal touch. Located in Kent County, you'll enjoy a peaceful retreat while still being close to local amenities. This property is not just a house; it's a place where you can truly feel at home. Don't miss the opportunity to make this inviting space your own! This property is being sold as-is.

4020 Eastern Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

350 Creekside Commons Ct, Stevensville
$385,000
2 Beds ⋅ 3 Baths
Kent Island Waterfront Living! Spectacular sunsets, breathtaking water views, and an exceptional location on Thompson Creek. Conveniently located just minutes from the Chesapeake Bay Bridge, Kent Island Medical Center and an abundance of fabulous waterfront restaurants, shopping and scenic parks. Discover your own peaceful waterfront retreat in Creekside Commons, where tranquility, privacy, and spectacular year-round water views take center stage. Perfectly positioned at the end of a quiet cul-de-sac, this desirable end-unit residence arguably offers one of the finest locations and floor plans in the entire community. Relax on your expansive waterfront deck and take in unforgettable sunsets over Thompson Creek or unwind on the charming wraparound front porch. With unobstructed water views instead of neighboring homes, this exceptional setting offers a wonderful sense of openness and serenity. The entire main level features beautiful recently finished 31/4-inch solid maple plank hardwood flooring, adding warmth and timeless elegance throughout. The kitchen is outfitted with contemporary white cabinetry, complete suite of brand-new Frigidaire Gallery stainless steel appliances, Quartz countertops, tile backsplash, a large box bay window including a counter-depth French-four door refrigerator. Upstairs you��ll find 2 almost 20' long bedrooms each with a spacious walk-in closet, another additional storage closet both en-suite with private bathrooms. Just about everything is new including plumbing fixtures, upstairs patterned carpet, paint, countertops and waterside bathroom vanity and LVT Flooring. Enjoy all the benefits of this beautiful waterfront setting with a remarkably affordable condominium homeowners association fee of just $175 per month. Why settle for views of neighboring homes when you can enjoy sweeping, unobstructed waterfront vistas and spectacular sunsets all year long. Owner is Agent.

350 Creekside Commons Ct, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

26989 Miles River Rd, Easton
$11,500,000
6 Beds ⋅ 7 Baths
Fairmiles, one of Talbot County’s most distinguished waterfront estates, enjoys an extraordinary setting along the coveted Miles River. This Federal-style manor blends timeless elegance with the warmth and charm of Maryland’s Eastern Shore. Rarely does an estate offer such an intimate connection to the water. The residence and waterside swimming pool are remarkably close to the protected shoreline, capturing sweeping, ever- changing river views from nearly every room. Each season unveils its own captivating beauty: summer yachts gracefully navigating the river, autumn’s brilliant palette of changing colors, the enchanting glow of Christmas trees illuminating with neighboring piers, and the fresh blossoms of spring. Together, these ever-changing scenes create a remarkable waterfront experience throughout the year. A private dock with an impressive eight feet of mean low water (MLW) depth offers exceptional opportunities for accommodating deep-draft vessels. Ideally situated between historic Easton and St. Michaels, Fairmiles combines privacy, natural beauty, and refined waterfront living with convenient access to exceptional dining, shopping, and cultural attractions. For the discerning traveler, Easton Airport is approximately ten minutes away, offering convenient private aviation access and fixed-base operator (FBO) services. By appointment only. Listing agents must accompany all showings. Do not enter the property without an appointment.

26989 Miles River Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact:

6119 Country Club Dr, Easton
$2,000,000
3 Beds ⋅ 4 Baths
Location, location, location. This fully renovated waterfront rancher sits on a 2+ acre, park-like lot bordering Talbot Country Club, just off the Oxford Road corridor — close enough to walk to lunch at the club, private enough to forget it's there. Inside, the home lives like a boutique retreat. The kitchen and family room combine around quartz counters, stainless appliances, and custom solid wood cabinetry, opening to a living room with fireplace and reclaimed barnwood oak flooring running through the main living areas. The primary suite channels a five-star hotel — custom built-ins, a tiled zero-entry shower, and a private steam shower. A tile-floored sunroom and thoughtful ADA/aging-in-place features (32"+ doorways, 36"+ halls, roll-in shower access) round out a home built for comfort at every stage of life. The mechanicals match the finishes: whole-home generator, upgraded electrical panel, whole-home Sonos audio across six zones (garage, front porch, living room, great room, back porch, and poolside), upgraded well pump for stronger water volume throughout, and an epoxy-finished, cabinet-outfitted garage. Outside, this is a waterman's and water-lover's dream. The private dock — rebuilt larger, with new water and electric service — includes two remote-controlled boat lifts, two remote-controlled jet ski lifts, and a floating kayak launch, all set on 150 feet of frontage with 3' MLW on Trippe Creek. Crabbing is easy right off the dock. The in-ground gunite pool sits shaded by mature trees, creating a private, cooler retreat even at the height of summer, with recently replaced pumps and upgraded floating sprinkler equipment. Enjoy sunrise from the back porch and sunset from the front — with front-row seats to the eagles and osprey that nest along the creek each year, arriving as early as March. This is more than a renovation — it's a fully re-system waterfront estate, ready for its next chapter.

6119 Country Club Dr, Easton

Listing courtesy of Real Broker, LLC - Chester. Contact:

148 Flagstaff Way Unit 2312, Chester
$599,990
2 Beds ⋅ 3 Baths
Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

148 Flagstaff Way Unit 2312, Chester

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

8014 Gosling Pond Ct, St Michaels
$775,000
4 Beds ⋅ 3 Baths
Beautifully situated on an exceptional lot overlooking a picturesque pond, this spacious home in the desirable Back Creek Landing community offers gorgeous sunset views, wonderful privacy, and a peaceful setting just minutes from historic St. Michaels. Tucked away on a quiet cul-de-sac, the property enjoys a lovely natural backdrop and a sense of tranquility that makes it feel like a private retreat. With over 3,000 square feet of living space, this thoughtfully designed home features 4 bedrooms, 2.5 baths, and a comfortable, versatile floor plan ideal for both everyday living and entertaining. Highlights include a spacious primary suite, inviting family room, separate dining room, and a private office or den. The eat-in kitchen, featuring newer appliances, opens to a delightful screened porch where you can relax, enjoy the pond views, and take in the spectacular evening sunsets. Beautifully maintained and thoughtfully updated, the home features fresh interior paint, an encapsulated crawl space, and numerous upgrades and special touches throughout. Generous living spaces and an easy flow between rooms create a welcoming atmosphere, with plenty of room to gather with family and friends or simply enjoy the comforts of home. Back Creek Landing is a charming community offering a wonderful Eastern Shore lifestyle, with amenities including a community pier on San Domingo Creek, kayak racks, scenic walking trails, ponds, and a wildlife observation area. Just a short drive away, historic St. Michaels offers an exceptional selection of waterfront dining, boutique shopping, marinas, and year-round activities. From quiet mornings overlooking the pond to spectacular sunsets from the screened porch, this is a home designed for enjoying the beauty and relaxed pace of life on Maryland’s Eastern Shore

8014 Gosling Pond Ct, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

5 S Park St S, Easton
$575,000
3 Beds ⋅ 2 Baths
This stunning Bungalow with a seperate commercial rental was beautifully renovated in 2020 and offers a perfect blend of modern luxury and timeless charm. With 1,168 sq. ft. of meticulously designed space in the residence, every corner of this home exudes warmth and sophistication. The renovated office building adds additional square footage. The open layout invites natural light, highlighting the exquisite craftsmanship throughout. Enjoy the seamless flow between indoor and outdoor living, perfect for entertaining or quiet evenings at home. The property features a versatile office/studio, ideal for remote work or creative pursuits. Nestled on a generous 0.19-acre lot, the lush surroundings provide a serene escape from the hustle and bustle of daily life. Parking is a breeze with ample driveway and street options. This residence is not just a home; it's a lifestyle, offering comfort, elegance, and a sense of community. Experience the joy of living in a space that has been thoughtfully updated to meet the demands of modern living while retaining its unique character. Your dream home and investment awaits!

5 S Park St S, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

200 High Thicket Ln, Stevensville
$1,800,000
4 Beds ⋅ 4 Baths
A RARE OPPORTUNITY TO OWN OVER 17 SPRAWLING ACRES ON KENT ISLAND! Discover the beauty, privacy, and endless possibilities of this extraordinary estate nestled in the picturesque countryside of Stevensville. Surrounded by nature, abundant wildlife, and beautiful water views, this stately Georgian Colonial offers over 4000 square feet of living space, including a spacious great room, generous living areas, a beautiful sunroom, an impressive office surrounded with built-ins, and a first-floor guest suite. Imagine starting your mornings with a cup of coffee in the sunroom, watching the sunrise over the water as herons glide across the shoreline and nature comes to life right outside your windows. It's the kind of peaceful setting that makes every day feel like a getaway! This remarkable property offers a horse barn, expansive grounds, and plenty of room to roam. Whether you're an equestrian enthusiast, nature lover, or simply seeking the peace and privacy of country estate living, this one-of-a-kind setting offers something truly special. Enjoy picturesque views of two tidal lakes and a canal leading to Eastern Bay, complete with your own private pier for launching kayaks, canoes, jet skis, and small boats. Outdoor living and entertaining are equally impressive! Relax by the in-ground swimming pool, pick fruit from the fruit trees, eat crabs on the screened in porch, enjoy the expansive deck or gather with family and friends in the outdoor kitchen and entertainment area, featuring a built-in grill, wet bar, granite countertops, and two TV connections—perfect for watching the big game while enjoying the beautiful surroundings. Extensive landscaping, multiple patios, and a picturesque view add to the charm and tranquility of this exceptional property. Offering a rare combination of acreage, equestrian amenities, waterfront recreation, and resort-style outdoor living, this sprawling estate is truly a special find on Kent Island. Enjoy the serenity of your own private retreat while remaining conveniently located near shopping, dining, marinas, and the Chesapeake Bay Bridge. An extraordinary property where peaceful mornings, unforgettable gatherings, and the beauty of nature become part of everyday life!

200 High Thicket Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

727 Warbler Way, Chester
$979,990
4 Beds ⋅ 4 Baths
Welcome to the Mykonos, a beautifully designed home that blends an open-concept floorplan with Classic-inspired style, creating the perfect balance of comfort and functionality. This spacious home features 4 bedrooms, 3.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

727 Warbler Way, Chester

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

244 Warbler Way, Chester
$700,000
2 Beds ⋅ 2 Baths
Welcome to 244 Warbler Way, a beautifully appointed Jenkins model built in 2025 and located in the sought-after 55+ community of Four Seasons at Kent Island. This thoughtfully designed 2-bedroom, 2-bath home offers stylish, low-maintenance living with upgrades throughout. Luxury vinyl plank flooring flows through the main living areas, leading to a bright, open-concept kitchen featuring upgraded finishes and a premium GE Café appliance package. The kitchen opens seamlessly to the dining and living spaces, creating an inviting layout perfect for both everyday living and entertaining. A beautiful propane fireplace anchors the living room, adding warmth and character to the heart of the home. Enjoy easy indoor-outdoor living from the screened porch or step outside to the hardscaped patio—an ideal setting for morning coffee, relaxing evenings, or entertaining friends. Built just last year, this home offers the benefits of newer construction without the wait. Located in Four Seasons at Kent Island, residents enjoy a vibrant 55+ lifestyle with resort-style amenities and a prime Eastern Shore location convenient to the Chesapeake Bay, shopping, dining, and the Bay Bridge. Move right in and enjoy everything this beautiful home and community have to offer!

244 Warbler Way, Chester

Listing courtesy of Samson Properties. Contact:

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