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****NEW PATH TO WATER FOR YOUR GATOR OR UTV**** This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect "magnet house" to attract friends and family or an amazing investment opportunity.

24050 Macs Ln, Worton

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

$395,000

Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

21712 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

11989 Augustine Herman Hwy, Kennedyville

$245,000

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

2 Baths

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,495,000

NEW YEAR ON IT’S WAY AND NOW IS TIME TO PLAN YOUR NEW LIFE. THIS FARM WOULD BER A GREAT PLACE TO START. ‘BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE. Narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments gives hunting sites spread throughout. Home was moved approx 20 years siting onto a new foundation then renovated to enjoy the views and ready for its new owners. Horses, we have some fencing, turn in shed, 4 stall to the rear of 3 level barn giving you plenty of room for storage of hay, straw and feed. And think how much fun to ride through and impoundment? Almost adjoins the 4,000 Millington Wildlife Preserve, with riding trails. Remember this area is protected from the surrounding farms becoming communities and the end of your dreams. Haven’t you work Hard all these Years? Reward yourself now with unique Opportunity while it’s available. LOOKING FOR EXTRA INCOME? RECENT ZONING CHANGE NOW PERMITS Farm Wedding SITE ** IMAGINE A NEW CLASIC BARN AND MAYBE EVEN A GAZIBO BOTH OVERLOOKING THE LARGEST POND INCLUDING LANDSCAPING, PARKING AND OTHER FEATURES TO THIS UNIQE PROPERTY. COOLEST THING, YOU ARE LANDLORD, LET WEDDING PLANNERS DEAL WITH REST. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

NEW YEAR ON IT’S WAY AND NOW IS TIME TO PLAN YOUR NEW LIFE. THIS FARM WOULD BER A GREAT PLACE TO START. ‘BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE. Narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments gives hunting sites spread throughout. Home was moved approx 20 years siting onto a new foundation then renovated to enjoy the views and ready for its new owners. Horses, we have some fencing, turn in shed, 4 stall to the rear of 3 level barn giving you plenty of room for storage of hay, straw and feed. And think how much fun to ride through and impoundment? Almost adjoins the 4,000 Millington Wildlife Preserve, with riding trails. Remember this area is protected from the surrounding farms becoming communities and the end of your dreams. Haven’t you work Hard all these Years? Reward yourself now with unique Opportunity while it’s available. LOOKING FOR EXTRA INCOME? RECENT ZONING CHANGE NOW PERMITS Farm Wedding SITE ** IMAGINE A NEW CLASIC BARN AND MAYBE EVEN A GAZIBO BOTH OVERLOOKING THE LARGEST POND INCLUDING LANDSCAPING, PARKING AND OTHER FEATURES TO THIS UNIQE PROPERTY. COOLEST THING, YOU ARE LANDLORD, LET WEDDING PLANNERS DEAL WITH REST. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

13235 Knotts Ln, Golts

Listing courtesy of Meredith Fine Properties. Contact:

$795,000

This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining. Hardwood flooring runs throughout the home. The main level offers a flexible layout with a bedroom just off the entry and a nearby full bath. The kitchen features double wall ovens and a gas cooktop in the island and opens to comfortable living spaces. The living room includes a gas fireplace, while the family room offers custom built-ins, a Vermont wood stove, and direct access to the courtyard and backyard. Upstairs, the primary suite includes a large bath with soaking tub, stall shower, and double vanity. A second en-suite bedroom currently serves as an office with extensive custom built-in cabinetry and could easily convert back to bedroom use. A mudroom off the attached two-car garage provides access to the side yard and leads to a staircase accessing a finished bonus room above the garage. This flexible space features independent heating and hot water and offers excellent options for guests, workspace, or additional living area. Custom built-ins are also found in the garage, family room, bedroom, and office. Additional improvements include a roof replacement in 2025, upgraded heating system in 2020, and a Rinnai hot water system. The property also features an irrigation system to maintain the beautifully landscaped grounds. Cooke’s Hope residents enjoy walking trails, tennis courts, fitness center, dog park, and well-maintained community green spaces.

4 Beds ⋅ 4 Baths

This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining. Hardwood flooring runs throughout the home. The main level offers a flexible layout with a bedroom just off the entry and a nearby full bath. The kitchen features double wall ovens and a gas cooktop in the island and opens to comfortable living spaces. The living room includes a gas fireplace, while the family room offers custom built-ins, a Vermont wood stove, and direct access to the courtyard and backyard. Upstairs, the primary suite includes a large bath with soaking tub, stall shower, and double vanity. A second en-suite bedroom currently serves as an office with extensive custom built-in cabinetry and could easily convert back to bedroom use. A mudroom off the attached two-car garage provides access to the side yard and leads to a staircase accessing a finished bonus room above the garage. This flexible space features independent heating and hot water and offers excellent options for guests, workspace, or additional living area. Custom built-ins are also found in the garage, family room, bedroom, and office. Additional improvements include a roof replacement in 2025, upgraded heating system in 2020, and a Rinnai hot water system. The property also features an irrigation system to maintain the beautifully landscaped grounds. Cooke’s Hope residents enjoy walking trails, tennis courts, fitness center, dog park, and well-maintained community green spaces.

28713 Emanuel St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$399,000

Welcome to an exceptional opportunity to own a home in the highly sought‑after Mulberry Station community. This spacious 4‑bedroom, 2.5‑bath residence offers one of the neighborhood’s most desirable floor plans, set on nearly a half‑acre—one of the largest lots in the community—and backing to peaceful open farmland for added privacy and views. Inside, the home features a welcoming flow featuring hardwood floors in the foyer with a formal living room, a separate family room enhanced by custom built‑in bookcases, an entertainment center, a gas fireplace with a slate hearth and Anderson windows throughout. The formal dining room sits just off the kitchen, which includes an Americast sink and plenty of workspace for everyday cooking or entertaining. Upstairs, the generous primary suite offers a relaxing retreat complete with a soaking tub, while three additional bedrooms provide ample space for family, guests, or a home office. Several areas of carpet have already been replaced, giving you a head start on updates. Outdoor living is just as appealing, with a rear deck overlooking wide‑open farmland—an ideal setting for morning coffee, evening sunsets, or weekend gatherings. A two‑car garage adds convenience and storage options. While the home does need some TLC, it is priced accordingly and presents tremendous potential for a buyer with vision. With its spacious layout, prime lot, and sought‑after location, this Mulberry Station property is a rare chance to create a home that truly reflects your style. The seller is selling in as-is condition and has priced the house accordingly as some updating will likely be needed. So much to offer, come see. Please see estimate and scope of repairs from the owner's contractor in documents section.

Welcome to an exceptional opportunity to own a home in the highly sought‑after Mulberry Station community. This spacious 4‑bedroom, 2.5‑bath residence offers one of the neighborhood’s most desirable floor plans, set on nearly a half‑acre—one of the largest lots in the community—and backing to peaceful open farmland for added privacy and views. Inside, the home features a welcoming flow featuring hardwood floors in the foyer with a formal living room, a separate family room enhanced by custom built‑in bookcases, an entertainment center, a gas fireplace with a slate hearth and Anderson windows throughout. The formal dining room sits just off the kitchen, which includes an Americast sink and plenty of workspace for everyday cooking or entertaining. Upstairs, the generous primary suite offers a relaxing retreat complete with a soaking tub, while three additional bedrooms provide ample space for family, guests, or a home office. Several areas of carpet have already been replaced, giving you a head start on updates. Outdoor living is just as appealing, with a rear deck overlooking wide‑open farmland—an ideal setting for morning coffee, evening sunsets, or weekend gatherings. A two‑car garage adds convenience and storage options. While the home does need some TLC, it is priced accordingly and presents tremendous potential for a buyer with vision. With its spacious layout, prime lot, and sought‑after location, this Mulberry Station property is a rare chance to create a home that truly reflects your style. The seller is selling in as-is condition and has priced the house accordingly as some updating will likely be needed. So much to offer, come see. Please see estimate and scope of repairs from the owner's contractor in documents section.

8804 Roundhouse Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$289,000

Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

3 Beds ⋅ 1 Baths

Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

4818 Piney Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$1,495,000

NEW YEAR IS FAST APPROACHING. HOW ABOUT YOU, TIME FOR A NEW BEGINNING? LOOKING FOR PRIVACY? Hidden away at the end of country lane Privacy awaits Surrounded by woods 106 Acres Hunting Farm in North East Kent County. regulation's insure surrounding farms will remain rather than growing communities. 1900 farm home renovated about 20 yrs. Ago including new heat pump. Three Bedrooms, 2 Full Baths, Dining Room, Living Room, Family Room with Fireplace. Enjoy the picturesque views of farm from 2nd floor deck off master bedroom Perfect setting for Canadian geese to spend the nights adding to your enjoyment. Some fencing 4 stalls behind the barn for horses plus a turn in shed. Many nice duck hunting properties are impacted by global warming rising sea level not an issue here. Elevation is well over 50 feet above sea level, so you a safe investment that can be enjoyed for generations to come. Featuring Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself..20 minutes from Middletown, De that offers sales tax free shopping and dining. WOULD YOU LIKE EXTRA INCOME? RECENT ZONING CHANGE PERMITS FARM WEDDINGS WITH COUNTY APPROVAL. IMAGINE A NEW CLASSIC BARN AND PERHAPS A GIZABO OVERLOOKING THE LARGEST POND? ADD IN A GREAT LANDSCAPING PARKING AND FEATURES FOR A DESIRABLE DESTINATION. WITH SO MANY PEOPLES SO CLOSE. COOL PART YOU ARE THE LANDLORD, LET WEDDING PLANER HANDLE THE REST. Wilmington, Towson & Bay Bridge about 50 minutes. Philadelphia and West Chester about 90 minutes. Almost adjoins the 4,000 Millington Wildlife Preserve. Google it to see what’s available. HERE IS YOUR CHANCE * STEP UP, AND ENJOY A GENERATIONAL TREASURE! Do not enter property without appointment and with Listing Agent. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

NEW YEAR IS FAST APPROACHING. HOW ABOUT YOU, TIME FOR A NEW BEGINNING? LOOKING FOR PRIVACY? Hidden away at the end of country lane Privacy awaits Surrounded by woods 106 Acres Hunting Farm in North East Kent County. regulation's insure surrounding farms will remain rather than growing communities. 1900 farm home renovated about 20 yrs. Ago including new heat pump. Three Bedrooms, 2 Full Baths, Dining Room, Living Room, Family Room with Fireplace. Enjoy the picturesque views of farm from 2nd floor deck off master bedroom Perfect setting for Canadian geese to spend the nights adding to your enjoyment. Some fencing 4 stalls behind the barn for horses plus a turn in shed. Many nice duck hunting properties are impacted by global warming rising sea level not an issue here. Elevation is well over 50 feet above sea level, so you a safe investment that can be enjoyed for generations to come. Featuring Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself..20 minutes from Middletown, De that offers sales tax free shopping and dining. WOULD YOU LIKE EXTRA INCOME? RECENT ZONING CHANGE PERMITS FARM WEDDINGS WITH COUNTY APPROVAL. IMAGINE A NEW CLASSIC BARN AND PERHAPS A GIZABO OVERLOOKING THE LARGEST POND? ADD IN A GREAT LANDSCAPING PARKING AND FEATURES FOR A DESIRABLE DESTINATION. WITH SO MANY PEOPLES SO CLOSE. COOL PART YOU ARE THE LANDLORD, LET WEDDING PLANER HANDLE THE REST. Wilmington, Towson & Bay Bridge about 50 minutes. Philadelphia and West Chester about 90 minutes. Almost adjoins the 4,000 Millington Wildlife Preserve. Google it to see what’s available. HERE IS YOUR CHANCE * STEP UP, AND ENJOY A GENERATIONAL TREASURE! Do not enter property without appointment and with Listing Agent. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

13235 Knotts, Golts

Listing courtesy of Meredith Fine Properties. Contact:

$785,000

Rose Cottage — The Home You Discover After a Perfect Day on the Water. A sailor arriving in Oxford often falls in love twice: first with the town, and then with the home that feels like it belongs to their journey. Rose Cottage is that home — a beautifully renovated, expanded Eastern Shore retreat nestled near marinas, Town Park, restaurants, and the quiet charm of Town Creek. After tying up at the Tred Avon Yacht Club, or one of several highly rated Oxford marinas, it’s an easy, scenic meander beneath shade trees and by historic cottages to your new home. That’s when Rose Cottage appears — welcoming, warm, and unmistakably connected to the sailing lifestyle. A Sailor’s Location — Everywhere That Matters. Rose Cottage sits in one of Oxford’s most desirable corridors: ● Short distance to the Tred Avon Yacht Club — ideal for regattas, junior sailing, or evening socials ● Minutes from Town Park, where sailors relax under the oaks after a day on the water ● Short promenade to Oxford’s marinas, boatyards, and waterfronts ● Close to local restaurants — from casual bites to fine dining ● Serene Town Creek views just a glance away, capturing the quiet beauty that makes Oxford unforgettable This is the rare home where you can finish a sail and be at your front door in minutes. Historic Charm, Modern Comfort. Inside, Rose Cottage blends its original character with a full structural renovation and a Christine Dayton designed 800 sq ft expansion completed in 2011–2012. The extended roofline, new primary bedroom, updated systems, and all-new flooring create a turnkey home that feels fresh, bright, and thoughtfully designed. The preserved street-facing windows maintain the cottage’s historic personality, while the newer windows and cementitious siding ensure long-term durability. A Home That Fits the Oxford Lifestyle. For sailors, cruisers, and anyone who loves the water, Rose Cottage offers something rare: a modernized home in a historic sailing town, near to everything that makes Oxford special. It’s the kind of place buyers don’t just choose — they discover.

Rose Cottage — The Home You Discover After a Perfect Day on the Water. A sailor arriving in Oxford often falls in love twice: first with the town, and then with the home that feels like it belongs to their journey. Rose Cottage is that home — a beautifully renovated, expanded Eastern Shore retreat nestled near marinas, Town Park, restaurants, and the quiet charm of Town Creek. After tying up at the Tred Avon Yacht Club, or one of several highly rated Oxford marinas, it’s an easy, scenic meander beneath shade trees and by historic cottages to your new home. That’s when Rose Cottage appears — welcoming, warm, and unmistakably connected to the sailing lifestyle. A Sailor’s Location — Everywhere That Matters. Rose Cottage sits in one of Oxford’s most desirable corridors: ● Short distance to the Tred Avon Yacht Club — ideal for regattas, junior sailing, or evening socials ● Minutes from Town Park, where sailors relax under the oaks after a day on the water ● Short promenade to Oxford’s marinas, boatyards, and waterfronts ● Close to local restaurants — from casual bites to fine dining ● Serene Town Creek views just a glance away, capturing the quiet beauty that makes Oxford unforgettable This is the rare home where you can finish a sail and be at your front door in minutes. Historic Charm, Modern Comfort. Inside, Rose Cottage blends its original character with a full structural renovation and a Christine Dayton designed 800 sq ft expansion completed in 2011–2012. The extended roofline, new primary bedroom, updated systems, and all-new flooring create a turnkey home that feels fresh, bright, and thoughtfully designed. The preserved street-facing windows maintain the cottage’s historic personality, while the newer windows and cementitious siding ensure long-term durability. A Home That Fits the Oxford Lifestyle. For sailors, cruisers, and anyone who loves the water, Rose Cottage offers something rare: a modernized home in a historic sailing town, near to everything that makes Oxford special. It’s the kind of place buyers don’t just choose — they discover.

228 South St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

$850,000

Nestled within the serene enclave of Goose Point Estates, this exquisite one level living home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This residence boasts a modern aesthetic while retaining its timeless charm. Step inside to discover a spacious 2,141 square feet of meticulously designed living space. The interior features a warm palette complemented by rich hardwood flooring and plush carpeting, creating an inviting atmosphere throughout. Crown moldings and chair railings add a touch of elegance, while recessed lighting and skylights bathe the space in natural light. The heart of the home is undoubtedly the gourmet kitchen, equipped with upgraded countertops and ample table space for casual dining. High-end appliances, including a self-cleaning oven, built-in microwave, and energy-efficient dishwasher, make cooking a delight. The adjacent family room, complete with a charming wood-burning fireplace, provides a perfect retreat for relaxation. This residence features four generously sized bedrooms, including a main-level bedroom for convenience. The luxurious master suite offers a walk-in closet and a spa-like bathroom with a stall shower included with a hot tub, ensuring a private oasis for unwinding after a long day. Outside, the property is equally impressive, set on a sprawling 2.4-acre lot surrounded by lush trees and serene woods, providing a tranquil backdrop for outdoor living. Enjoy evenings under the stars in the hot tub or host gatherings with friends in the beautifully landscaped yard. The exterior is adorned with thoughtful features such as bump-outs, exterior lighting, and flood lights, enhancing both functionality and aesthetics. Additional highlights include a spacious attached garage with extra storage, main-floor laundry for added convenience, and a water treatment system for peace of mind. This home is not just a residence; it's a lifestyle choice, offering a perfect blend of luxury, comfort, and nature. Experience the best of both worlds in this exceptional property, where modern amenities meet the tranquility of nature, creating a perfect sanctuary to call home. Roof is 10 years old. Goose Point Estates is just minutes away from route 50 and the Chesapeake Bay Bridge but far enough away from all the traffic.

Nestled within the serene enclave of Goose Point Estates, this exquisite one level living home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This residence boasts a modern aesthetic while retaining its timeless charm. Step inside to discover a spacious 2,141 square feet of meticulously designed living space. The interior features a warm palette complemented by rich hardwood flooring and plush carpeting, creating an inviting atmosphere throughout. Crown moldings and chair railings add a touch of elegance, while recessed lighting and skylights bathe the space in natural light. The heart of the home is undoubtedly the gourmet kitchen, equipped with upgraded countertops and ample table space for casual dining. High-end appliances, including a self-cleaning oven, built-in microwave, and energy-efficient dishwasher, make cooking a delight. The adjacent family room, complete with a charming wood-burning fireplace, provides a perfect retreat for relaxation. This residence features four generously sized bedrooms, including a main-level bedroom for convenience. The luxurious master suite offers a walk-in closet and a spa-like bathroom with a stall shower included with a hot tub, ensuring a private oasis for unwinding after a long day. Outside, the property is equally impressive, set on a sprawling 2.4-acre lot surrounded by lush trees and serene woods, providing a tranquil backdrop for outdoor living. Enjoy evenings under the stars in the hot tub or host gatherings with friends in the beautifully landscaped yard. The exterior is adorned with thoughtful features such as bump-outs, exterior lighting, and flood lights, enhancing both functionality and aesthetics. Additional highlights include a spacious attached garage with extra storage, main-floor laundry for added convenience, and a water treatment system for peace of mind. This home is not just a residence; it's a lifestyle choice, offering a perfect blend of luxury, comfort, and nature. Experience the best of both worlds in this exceptional property, where modern amenities meet the tranquility of nature, creating a perfect sanctuary to call home. Roof is 10 years old. Goose Point Estates is just minutes away from route 50 and the Chesapeake Bay Bridge but far enough away from all the traffic.

121 Eareckson Ln, Stevensville

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

$410,000

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

21406 Dogwood Cove Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

$1,995,000

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

9020 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$239,900

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

104 Conley Dr, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

$160,000

Lot has been approved by the Historic commission and exterior plans available , Easton Board of zoning appeal is approved for Variances to lot lines setback and approved for Duplex of up to 1200 feet per unit .Off street parking approved by BOZA for two cars.. Lane Engineering approved drawings available...Easton Utilities has approved all services to lot......Sidewalks and curb already completed on site. Property fronts on Aurora Street and South Lane ...Exterior plans approved by Historic Commission and BUYER needs to file final interior plans to town for building permits......No impact fees paid to date......A Great Investment property in the heart of Easton

20 S Aurora, Easton

Listing courtesy of Stafford-Stafford Real Estate. Contact:

$324,900

MAJOR PRICE IMPROVEMENT! Discover this updated home that blends classic architecture with modern living, offering 1,783 sq. ft. of versatile space. Venture inside to find a welcoming traditional floor plan with new luxury vinyl plank flooring and fresh interior paint that flows from the living room to dining room and well-appointed bedrooms. The upgraded kitchen, equipped with white shaker cabinetry, stainless-steel appliances and granite countertops, is a perfect place for culinary enthusiasts. The three bedrooms and full bathroom equipped with a stall shower and whirlpool tub, ensures comfort and relaxation after a long day. The finished 2nd level with new carpet flooring can be converted or used into a 4th bedroom while the main level sunroom with its bright airy ambience is a perfect spot for entertaining. Outside, enjoy the tranquility of your front and rear yards, great for gardening or outdoor activities.

4 Beds ⋅ 2 Baths

MAJOR PRICE IMPROVEMENT! Discover this updated home that blends classic architecture with modern living, offering 1,783 sq. ft. of versatile space. Venture inside to find a welcoming traditional floor plan with new luxury vinyl plank flooring and fresh interior paint that flows from the living room to dining room and well-appointed bedrooms. The upgraded kitchen, equipped with white shaker cabinetry, stainless-steel appliances and granite countertops, is a perfect place for culinary enthusiasts. The three bedrooms and full bathroom equipped with a stall shower and whirlpool tub, ensures comfort and relaxation after a long day. The finished 2nd level with new carpet flooring can be converted or used into a 4th bedroom while the main level sunroom with its bright airy ambience is a perfect spot for entertaining. Outside, enjoy the tranquility of your front and rear yards, great for gardening or outdoor activities.

205 Bryantown Lndg, Queenstown

Listing courtesy of Century 21 Downtown. Contact:

$595,000

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

2 Beds ⋅ 3 Baths

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit 43, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$513,000

Hillsboro model in the desirable Easton Club East 55+ Community. Corner lot! Over 3000sqft with a thoughtful floor plan. The first floor boasts the primary bedroom with a connected bathroom and large closet, guest bedroom and bathroom, an office/library, family room off of the eat in kitchen, living and dining room and large laundry room. Upstairs is a large loft area with a 3rd bedroom and full bathroom. Neutral colors. New HVAC in 2022, New roof in 2023. Seller is offering $5,000 towards new kitchen appliances!

Hillsboro model in the desirable Easton Club East 55+ Community. Corner lot! Over 3000sqft with a thoughtful floor plan. The first floor boasts the primary bedroom with a connected bathroom and large closet, guest bedroom and bathroom, an office/library, family room off of the eat in kitchen, living and dining room and large laundry room. Upstairs is a large loft area with a 3rd bedroom and full bathroom. Neutral colors. New HVAC in 2022, New roof in 2023. Seller is offering $5,000 towards new kitchen appliances!

7316 Casey Ave, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

$814,990

The Brentwood: True Executive-Style Luxury on the Eastern Shore Experience unparalleled scale and sophisticated design in the Brentwood, a magnificent 3,736-square-foot executive residence designed for modern luxury living. Set within a premier community featuring expansive, large home sites, this estate offers a rare and highly coveted feature for the Eastern Shore: a massive, full unfinished basement providing endless potential for future customization, a home gym, or unparalleled storage. The architectural design prioritizes ultimate privacy and comfort, boasting spacious bedrooms, each complete with its own private, dedicated en-suite bath. The crowning jewel of the home is the sprawling Owner’s Suite—a private sanctuary featuring an exclusive owner's sitting room, a massive walk-in closet, and a specialized wardrobe storage area designed for the ultimate organizer.Designed to blend grand indoor living with the coastal lifestyle, the Brentwood offers flexible structural options, including a sun-drenched morning room or a spacious three-car garage. Step outside to create your own private outdoor oasis on a generous home site, all while being just minutes from the scenic river for premier boating, kayaking, and outdoor water activities. The Brentwood isn’t just a home; it’s an elevated lifestyle. Feature & Highlight Lists 🌟 Executive Structural Highlights Massive Footprint: 3,736 sq. ft. of expertly designed, wide-open living space. The Eastern Shore Unicorn: Rare, full unfinished basement offering incredible structural storage or future finished square footage. Ultimate Family/Guest Privacy: Every single bedroom features its own private, dedicated en-suite bathroom. Flexible Footprint: Customization options to add a bright, open morning room or expand to a 3-car garage. The Owner’s Retreat Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. 🌊 Community & Lifestyle Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). Scenic River Access: Located just minutes from the river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. The Owner’s Retreat Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. 🌊 Community & Lifestyle Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). Scenic River Access: Located just minutes from the scenic Wye river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. "Limited time" Up to $20,000 closing cost assistance if buyer uses a Koch Homes preferred lender and tile company. Talbot County maintains the communities shared treatment facility.. The other fee listed reflects the public works facility fee (sewer fee)for ongoing operation, maintenance, administration and engineering.

4 Beds ⋅ 5 Baths

The Brentwood: True Executive-Style Luxury on the Eastern Shore Experience unparalleled scale and sophisticated design in the Brentwood, a magnificent 3,736-square-foot executive residence designed for modern luxury living. Set within a premier community featuring expansive, large home sites, this estate offers a rare and highly coveted feature for the Eastern Shore: a massive, full unfinished basement providing endless potential for future customization, a home gym, or unparalleled storage. The architectural design prioritizes ultimate privacy and comfort, boasting spacious bedrooms, each complete with its own private, dedicated en-suite bath. The crowning jewel of the home is the sprawling Owner’s Suite—a private sanctuary featuring an exclusive owner's sitting room, a massive walk-in closet, and a specialized wardrobe storage area designed for the ultimate organizer.Designed to blend grand indoor living with the coastal lifestyle, the Brentwood offers flexible structural options, including a sun-drenched morning room or a spacious three-car garage. Step outside to create your own private outdoor oasis on a generous home site, all while being just minutes from the scenic river for premier boating, kayaking, and outdoor water activities. The Brentwood isn’t just a home; it’s an elevated lifestyle. Feature & Highlight Lists 🌟 Executive Structural Highlights Massive Footprint: 3,736 sq. ft. of expertly designed, wide-open living space. The Eastern Shore Unicorn: Rare, full unfinished basement offering incredible structural storage or future finished square footage. Ultimate Family/Guest Privacy: Every single bedroom features its own private, dedicated en-suite bathroom. Flexible Footprint: Customization options to add a bright, open morning room or expand to a 3-car garage. The Owner’s Retreat Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. 🌊 Community & Lifestyle Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). Scenic River Access: Located just minutes from the river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. The Owner’s Retreat Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. 🌊 Community & Lifestyle Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). Scenic River Access: Located just minutes from the scenic Wye river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. "Limited time" Up to $20,000 closing cost assistance if buyer uses a Koch Homes preferred lender and tile company. Talbot County maintains the communities shared treatment facility.. The other fee listed reflects the public works facility fee (sewer fee)for ongoing operation, maintenance, administration and engineering.

0000 Rustling Oaks Dr, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact:

$990,000

Farm Compound., with three homes! Each home is independent with separate addresses, all on 48 acres. The lands include woods and a pond. The primary home is 2800 square feet just recently remodeled. Open concept living all the rooms are very spacious with a kitchen with tons of storage and lots of counter space. There is an office space as well so many options to use as additional bedrooms or hobby room. A laundry area that is a room not a closet. The HVAC system was just replaced on the main home, as many other features of this house. Number two house was just put on the property in 2025, Clayton Holmes three bedrooms two baths would make a wonderful in-laws house or a rental. Number three house sits to the back of the property again is its own separate structure, is a remodled single wide. Would make an excellent income, Property or a caretaker residence. This property offers so many options it’s unlimited. It also includes a 30 x 50 insulated pole barn with a concrete floor electric separate meter and pitcher pump. Two pasture areas exist with shelter for live stock they currently have goats. This is a absolutly one of a kind property if you want to have a Equine center lots of room to build a indoor arena or to raise livestock. The entire family can live here and have there own house. Would be an excellent Equine center good pastures building could be converted to stalls. The current owners have greatly improved the property it is now waiting for the next care takers to see what they do with this special property and its new use. Woods are currently getting selectively cut.

Farm Compound., with three homes! Each home is independent with separate addresses, all on 48 acres. The lands include woods and a pond. The primary home is 2800 square feet just recently remodeled. Open concept living all the rooms are very spacious with a kitchen with tons of storage and lots of counter space. There is an office space as well so many options to use as additional bedrooms or hobby room. A laundry area that is a room not a closet. The HVAC system was just replaced on the main home, as many other features of this house. Number two house was just put on the property in 2025, Clayton Holmes three bedrooms two baths would make a wonderful in-laws house or a rental. Number three house sits to the back of the property again is its own separate structure, is a remodled single wide. Would make an excellent income, Property or a caretaker residence. This property offers so many options it’s unlimited. It also includes a 30 x 50 insulated pole barn with a concrete floor electric separate meter and pitcher pump. Two pasture areas exist with shelter for live stock they currently have goats. This is a absolutly one of a kind property if you want to have a Equine center lots of room to build a indoor arena or to raise livestock. The entire family can live here and have there own house. Would be an excellent Equine center good pastures building could be converted to stalls. The current owners have greatly improved the property it is now waiting for the next care takers to see what they do with this special property and its new use. Woods are currently getting selectively cut.

420 Duhamel Corner Rd, Marydel

Listing courtesy of Benson & Mangold, LLC.. Contact:

$245,000

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$75,000

APPROVED PERMITS in hand for a 3 bedroom 2 bath home with full basement! Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.

Fairlee Road, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$79,000

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

2 Beds ⋅ 1 Baths

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact:

$275,000

Enjoy the convenience of townhome living in Oak Hollow, just minutes from historic downtown Chestertown, local schools, and the YMCA. With approximately 1,900 square feet of living space across three levels, this home offers a flexible layout with room to make it your own. The ground level features a versatile bonus room that could serve as a home office, workout space, or recreation room, along with an attached one-car garage. Upstairs, the main living level offers a spacious living room and an eat-in kitchen with access to a private rear deck overlooking a wooded backdrop—an inviting spot to relax or enjoy your morning coffee. The upper level includes three bedrooms, including a primary suite with a private bath, plus a convenient dedicated laundry area. The Seller is offering a $2,500 credit toward painting, cosmetic updates, or carpet, giving the next owner an opportunity to personalize the space to suit their style. Conveniently located and offering a practical, three-level layout, this Oak Hollow townhome is worth a look for buyers seeking their first home, those looking to downsize, or investors exploring rental opportunities.

Enjoy the convenience of townhome living in Oak Hollow, just minutes from historic downtown Chestertown, local schools, and the YMCA. With approximately 1,900 square feet of living space across three levels, this home offers a flexible layout with room to make it your own. The ground level features a versatile bonus room that could serve as a home office, workout space, or recreation room, along with an attached one-car garage. Upstairs, the main living level offers a spacious living room and an eat-in kitchen with access to a private rear deck overlooking a wooded backdrop—an inviting spot to relax or enjoy your morning coffee. The upper level includes three bedrooms, including a primary suite with a private bath, plus a convenient dedicated laundry area. The Seller is offering a $2,500 credit toward painting, cosmetic updates, or carpet, giving the next owner an opportunity to personalize the space to suit their style. Conveniently located and offering a practical, three-level layout, this Oak Hollow townhome is worth a look for buyers seeking their first home, those looking to downsize, or investors exploring rental opportunities.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$525,000

Just reduced to $525,000—affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investments—a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows—mean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1.

2 Beds ⋅ 1 Baths

Just reduced to $525,000—affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investments—a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows—mean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact:

$550,000

Absolutely Charming Eastern Shore Home with Beautiful Farm Views! Experience the peaceful charm of Queenstown living in this beautifully updated home situated on a gorgeous .83 acre lot surrounded by the natural beauty of Maryland’s Eastern Shore. Enjoy the slower pace of life with open farmland views, plenty of outdoor space, and a setting that feels away from the congestion while still being convenient to nearby shopping, restaurants, waterfront areas, and commuter routes. The welcoming front porch is the perfect place to relax and take in the scenic farm views, while the screened porch overlooking the backyard provides another wonderful space to enjoy the outdoors. Inside, this home is full of warmth and character with luxury vinyl plank flooring throughout the main level and thoughtful updates throughout. The upgraded kitchen features white cabinetry, stainless steel appliances, and a convenient laundry room nearby. The inviting family room offers a cozy wood burning fireplace, creating a comfortable gathering space. A main level office with a beautiful French door entry offers flexibility and could also serve as an additional bedroom, guest space, or hobby room. Upstairs, you will find three spacious bedrooms with fresh carpeting, including the impressive primary suite featuring a large ensuite bathroom, walk-in shower, dual sink vanity, and generous closet space. The additional bathrooms have also been beautifully updated. With abundant parking, nearly an acre of land, peaceful surroundings, and views that capture the best of Eastern Shore living, this Queenstown charmer is truly a special place to call home.

Absolutely Charming Eastern Shore Home with Beautiful Farm Views! Experience the peaceful charm of Queenstown living in this beautifully updated home situated on a gorgeous .83 acre lot surrounded by the natural beauty of Maryland’s Eastern Shore. Enjoy the slower pace of life with open farmland views, plenty of outdoor space, and a setting that feels away from the congestion while still being convenient to nearby shopping, restaurants, waterfront areas, and commuter routes. The welcoming front porch is the perfect place to relax and take in the scenic farm views, while the screened porch overlooking the backyard provides another wonderful space to enjoy the outdoors. Inside, this home is full of warmth and character with luxury vinyl plank flooring throughout the main level and thoughtful updates throughout. The upgraded kitchen features white cabinetry, stainless steel appliances, and a convenient laundry room nearby. The inviting family room offers a cozy wood burning fireplace, creating a comfortable gathering space. A main level office with a beautiful French door entry offers flexibility and could also serve as an additional bedroom, guest space, or hobby room. Upstairs, you will find three spacious bedrooms with fresh carpeting, including the impressive primary suite featuring a large ensuite bathroom, walk-in shower, dual sink vanity, and generous closet space. The additional bathrooms have also been beautifully updated. With abundant parking, nearly an acre of land, peaceful surroundings, and views that capture the best of Eastern Shore living, this Queenstown charmer is truly a special place to call home.

223 Overlook Dr, Queenstown

Listing courtesy of Douglas Realty LLC. Contact:

$1,500,000

Great location for your commercial development project! This 3.4 acres property is located across from the Bay Bridge Airport and is less than a mile from Rt. 50/301 and the Chesapeake Bay Bridge. With 304 ft of frontage on Rt. 8/Romancoke Road and over 700 ft along Kent Manor Drive, the property offers exceptional visibility with high traffic counts. It’s zoned Urban Commercial with access to public water and sewer service.

Romancoke Rd, Stevensville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$1,100,000

Unique opportunity to expand or start your business just minutes from the Eastern Shore thoroughfares of Routes 301 and 213 and also just outside of downtown Chestertown. The blend of infrastructure and zoning such as public sewer, Industrial zoning, tractor trailer access, railway abutting the business park and 3 phase electric throughout the building make this irresistible for a wide variety of businesses. Iconic Eastern Shore architect Peter Newlin designed the building with passive solar heating and cooling in mind as evidenced in the dynamic roof pitch. Radiant floor heating ensures that not only are your employees happy but your machines and materials are better protected as well. The layout allows for great separation of personnel, office tasks, and shop space. 3 Bathrooms, one with shower, allow for the staff to have their space of their own without sacrificing customer experience. Quality control, conference and storage rooms are thoughtfully planned out and spacious. The exterior provides ample parking for staff and customers separately while also designed for tractor trailor turnaround. Over 2 acres and extra sewer allotment allow for vision and future possibilities. Less than 2 hours from Philadelphia, Wilmington, Baltimore, and Washington DC. Opportunities like this don't come up often so jump in now for the growth of the Eastern Shore.

25416 Commerce Ln, Chestertown

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

$355,000

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a 4th bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a 4th bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

408 Crowberry Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$2,450,000

This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. The property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence features an open floor plan designed to capture panoramic water views. The spacious kitchen includes quartz countertops, stainless steel appliances, a large center island, beverage bar and dining area. A dramatic waterside family room showcases cathedral ceilings, exposed beam, skylights, a gas fireplace and floor-to-ceiling windows overlooking the creek and surrounding farmland. This stunning home further features a separate living room, waterfront primary suite, three additional bedrooms, a waterside office, an attached oversized two-car garage and so much more. Outdoor amenities include a waterside patio, in-ground waterside pool with extensive hardscaping and a private dock with electric and boat lift providing access to the Chesapeake Bay and its surrounding tributaries. A separate 2,700± sqft guest house with 3-4 bedrooms and 2.5 baths offers flexible accommodations for family, guests or short/long-term rental opportunities. Multiple barns and outbuildings provide endless possibilities for storage, livestock, equipment, hobbies or recreation. For outdoor enthusiasts, the acreage supports abundant wildlife including deer, turkey and geese, while the waterfront setting offers endless opportunities for boating, fishing, kayaking and exploring the Rivers, Creeks and Bay. This is a rare opportunity to own a waterfront estate just minutes from the shops, restaurants and maritime charm of St. Michaels. This is Eastern Shore living at its finest.

This stunning waterfront estate is located just minutes from Historic downtown St. Michaels and offers breathtaking views across Leadenham Creek. The property combines a beautifully renovated main residence, guest house, private dock, waterside pool and expansive open land in one exceptional Eastern Shore offering. Renovated in 2017, the 3,500± sqft brick residence features an open floor plan designed to capture panoramic water views. The spacious kitchen includes quartz countertops, stainless steel appliances, a large center island, beverage bar and dining area. A dramatic waterside family room showcases cathedral ceilings, exposed beam, skylights, a gas fireplace and floor-to-ceiling windows overlooking the creek and surrounding farmland. This stunning home further features a separate living room, waterfront primary suite, three additional bedrooms, a waterside office, an attached oversized two-car garage and so much more. Outdoor amenities include a waterside patio, in-ground waterside pool with extensive hardscaping and a private dock with electric and boat lift providing access to the Chesapeake Bay and its surrounding tributaries. A separate 2,700± sqft guest house with 3-4 bedrooms and 2.5 baths offers flexible accommodations for family, guests or short/long-term rental opportunities. Multiple barns and outbuildings provide endless possibilities for storage, livestock, equipment, hobbies or recreation. For outdoor enthusiasts, the acreage supports abundant wildlife including deer, turkey and geese, while the waterfront setting offers endless opportunities for boating, fishing, kayaking and exploring the Rivers, Creeks and Bay. This is a rare opportunity to own a waterfront estate just minutes from the shops, restaurants and maritime charm of St. Michaels. This is Eastern Shore living at its finest.

7543 Bozman Neavitt Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

$570,000

OVER 5 ACRES. NO HOA. JUST MINUTES FROM US301. That’s a combination that’s becoming increasingly difficult to find. Welcome to 913 Clark Corners Rd, where 5.42 ACRES of partially wooded land offer the freedom to live your way! Whether you’re dreaming of horses, chickens, gardening, recreational activities, frequent sightings of deer, birds, owls, and other wildlife, or simply room to breathe, this property delivers the space and flexibility today’s buyers are searching for. Inside, you’ll find a thoughtfully updated home featuring a fully renovated kitchen with quartz countertops, 42” soft-close white cabinetry, stainless steel appliances, recessed lighting, a large center island with seating, and luxury vinyl plank flooring that flows seamlessly into the spacious family room with a gas fireplace. The main level also boasts engineered hardwood floors and offers formal living and dining rooms, an updated powder room, and a renovated laundry/mud room with additional cabinetry, countertop workspace, and valuable pantry storage. Upstairs, the spacious primary suite includes a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide room for family, guests, hobbies, or a home office. Outside, enjoy a welcoming wraparound front porch that’s perfect for relaxing and taking in the peaceful surroundings, along with a rear deck, partially fenced backyard, large storage shed, mature landscaping, permanent Govee front exterior lighting, and a blend of open yard and wooded acreage that creates a setting rarely found at this price point. Above the garage, the unfinished attic space provides exceptional storage and potential future possibilities, subject to buyer verification of county requirements and approvals. Whether you’re looking for room to grow, room to roam, or simply room to breathe, this property delivers! Motivated sellers, home sold As Is!