easternshoremdfineproperties.com Search Results

Welcome to 30300 Kings Meadow Place! This spacious home is what peaceful country living is all about! Located on 1.5 acres just outside Easton town limits, you will enjoy nature at its best. A beautiful 3200+ sq. ft. home loaded with amenities - wood floors throughout the main level, with a recently renovated kitchen that now boasts an open floorplan to the Living room with a gas fireplace surrounded by built-in bookcases & Breakfast area with direct access to the rear covered porch. You will enjoy Quartz countertops, stainless steel appliances including a gas oven/range to prepare your meals that you can serve in the large formal dining room for those special guests. The Primary bedroom is located on the opposite side of the house than the other bedrooms for privacy & boasts a spacious spa-like bath, double walk-in closet and access to the rear covered porch. Two additional en-suite bedrooms on the main floor and a powder room give your guests or other family members their own privacy! A main floor fully-equipped laundry room is ideal! Did I mention that there is a covered front porch as well? Upstairs you will find a spacious loft that overlooks the kitchen which can be a whatever you desire - a family room, an office, a workout space. Also you will find the 4th bedroom and another room that could be a game room or play room. There is lots of storage in the house but you will love the attached 3 car garage with a workbench and even more storage. Currently there is no pool but there is certainly plenty of room to add one! If you are in the market for a lovely home in a peaceful country setting, you don't want to miss this one! Some of the furnishings may be purchased separately as well as great Harley Davidson motorcycle!

4 Beds ⋅ 4 Baths

Welcome to 30300 Kings Meadow Place! This spacious home is what peaceful country living is all about! Located on 1.5 acres just outside Easton town limits, you will enjoy nature at its best. A beautiful 3200+ sq. ft. home loaded with amenities - wood floors throughout the main level, with a recently renovated kitchen that now boasts an open floorplan to the Living room with a gas fireplace surrounded by built-in bookcases & Breakfast area with direct access to the rear covered porch. You will enjoy Quartz countertops, stainless steel appliances including a gas oven/range to prepare your meals that you can serve in the large formal dining room for those special guests. The Primary bedroom is located on the opposite side of the house than the other bedrooms for privacy & boasts a spacious spa-like bath, double walk-in closet and access to the rear covered porch. Two additional en-suite bedrooms on the main floor and a powder room give your guests or other family members their own privacy! A main floor fully-equipped laundry room is ideal! Did I mention that there is a covered front porch as well? Upstairs you will find a spacious loft that overlooks the kitchen which can be a whatever you desire - a family room, an office, a workout space. Also you will find the 4th bedroom and another room that could be a game room or play room. There is lots of storage in the house but you will love the attached 3 car garage with a workbench and even more storage. Currently there is no pool but there is certainly plenty of room to add one! If you are in the market for a lovely home in a peaceful country setting, you don't want to miss this one! Some of the furnishings may be purchased separately as well as great Harley Davidson motorcycle!

30300 Kings Meadow Pl, Easton

Listing courtesy of Shore Living Real Estate. Contact:

$949,000

Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a first‑floor primary suite with an ensuite spa bath, custom shower, and generous walk‑in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1‑car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you’ll enjoy easy access to charming shops, restaurants, waterfront activities, and year‑round festivals.

4 Beds ⋅ 3 Baths

Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a first‑floor primary suite with an ensuite spa bath, custom shower, and generous walk‑in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1‑car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you’ll enjoy easy access to charming shops, restaurants, waterfront activities, and year‑round festivals.

111 Chesapeake Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

$370,000

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

4 Beds ⋅ 3 Baths

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

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

$450,000

Mixed-use commercial property offering exceptional exposure in a sought-after location. The first floor commercial space features about 1800+ sq' separated between a large retail space, office/kitchen , and storage space. The second floor includes a 2-bedroom, 1-bath apartment—ideal for owner occupancy or rental income. Seller financing may be available for buyers with 20% down, 5% interest, amortized at 15 years with a 5 year balloon. The building offers flexible layout potential and is truly ready for your vision. Downstairs can easily be divided into three sections to rent out separately. Situated on nearly a half-acre lot, the property boasts a generous parking area with 12+ spaces and room for future expansion. A rare opportunity for entrepreneurs, investors, or owner-operators looking to establish or grow their business in the heart of Centreville. Take advantage of the seller financing opportunity and 5% rate!

2 Beds ⋅ 3 Baths

Mixed-use commercial property offering exceptional exposure in a sought-after location. The first floor commercial space features about 1800+ sq' separated between a large retail space, office/kitchen , and storage space. The second floor includes a 2-bedroom, 1-bath apartment—ideal for owner occupancy or rental income. Seller financing may be available for buyers with 20% down, 5% interest, amortized at 15 years with a 5 year balloon. The building offers flexible layout potential and is truly ready for your vision. Downstairs can easily be divided into three sections to rent out separately. Situated on nearly a half-acre lot, the property boasts a generous parking area with 12+ spaces and room for future expansion. A rare opportunity for entrepreneurs, investors, or owner-operators looking to establish or grow their business in the heart of Centreville. Take advantage of the seller financing opportunity and 5% rate!

305 E Water St, Centreville

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

$369,900

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

13831 Augustine Herman Hwy, Galena

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

$499,900

***BRAND NEW & MOVE-IN READY*** this spacious ranch home offers easy one level living and features high end finishes throughout, including a gourmet kitchen with stylish white and timber cabinetry, satin bronze hardware, quartz countertops, subway tile backsplash, and stainless steels appliances including a double oven, gas cooktop and range hood. The living room features a gas fireplace and large picture windows, providing an abundance of natural light. The owner's suite is equipped with a walk-in closet and luxurious bath with dual vanity, spacious shower w/dual shower heads and tile surround. Rounding out the main level is two additional bedrooms and a full bath with ceramic tile flooring and surround. Additional amenities include 9' ceilings, two car side load garage, LVP flooring, ceramic tile in all baths and laundry room, public sewer (no private septic), 30 year architectural shingles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, and a spacious front porch. All of this in a convenient location in close proximity to both downtown Saint Michaels and Easton shops, restaurants and grocery. NO HOA or restrictive covenants. Schedule your private tour today!

3 Beds ⋅ 3 Baths

***BRAND NEW & MOVE-IN READY*** this spacious ranch home offers easy one level living and features high end finishes throughout, including a gourmet kitchen with stylish white and timber cabinetry, satin bronze hardware, quartz countertops, subway tile backsplash, and stainless steels appliances including a double oven, gas cooktop and range hood. The living room features a gas fireplace and large picture windows, providing an abundance of natural light. The owner's suite is equipped with a walk-in closet and luxurious bath with dual vanity, spacious shower w/dual shower heads and tile surround. Rounding out the main level is two additional bedrooms and a full bath with ceramic tile flooring and surround. Additional amenities include 9' ceilings, two car side load garage, LVP flooring, ceramic tile in all baths and laundry room, public sewer (no private septic), 30 year architectural shingles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, and a spacious front porch. All of this in a convenient location in close proximity to both downtown Saint Michaels and Easton shops, restaurants and grocery. NO HOA or restrictive covenants. Schedule your private tour today!

26542 Royal Oak Rd, Easton

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

$487,000

SELLER-PAID 2-1 INTEREST RATE BUYDOWN AVAILABLE! Make homeownership more affordable with lower mortgage payments for the first two years! For example, based on an assumed 7.75% interest rate, buyers could enjoy a 5.75% rate in Year 1 (approximately $500/month savings), 6.75% in Year 2 (approximately $250/month savings), and 7.75% beginning in Year 3. That’s potentially $9,000 in savings over the first two years! Buyers may also have the opportunity to refinance if rates decrease, although refinancing is not guaranteed. Example only. Actual rates, payments, savings, and eligibility depend on loan terms and lender approval. Buyers must qualify at the full note rate, subject to lender requirements. Contact your lender for details. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

3 Beds ⋅ 3 Baths

SELLER-PAID 2-1 INTEREST RATE BUYDOWN AVAILABLE! Make homeownership more affordable with lower mortgage payments for the first two years! For example, based on an assumed 7.75% interest rate, buyers could enjoy a 5.75% rate in Year 1 (approximately $500/month savings), 6.75% in Year 2 (approximately $250/month savings), and 7.75% beginning in Year 3. That’s potentially $9,000 in savings over the first two years! Buyers may also have the opportunity to refinance if rates decrease, although refinancing is not guaranteed. Example only. Actual rates, payments, savings, and eligibility depend on loan terms and lender approval. Buyers must qualify at the full note rate, subject to lender requirements. Contact your lender for details. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

16 Howell Point Rd, Betterton

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

$375,000

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed.

2 Beds ⋅ 2 Baths

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed.

224 Ewingtown Rd, Church Hill

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$259,000

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

3 Beds ⋅ 2 Baths

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

115 Chester Arms Dr, Chestertown

Listing courtesy of Samson Properties. Contact:

$599,990

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!! Don’t miss this incredible opportunity—3 Car Garage! 4 bedrooms, 3.5 baths, offering exceptional space and value for today’s lifestyle. Backing to trees for added privacy and a serene view, this home delivers both comfort and setting. The bright sunroom off the kitchen creates the perfect gathering space, while the kitchen itself shines with a farmhouse sink, white cabinetry, quartz countertops, and a gourmet stainless steel appliance package with a hood. Luxury vinyl plank flooring spans the main level. Upstairs, enjoy the convenience of a second-level laundry room with a utility sink. Located in Trappe, MD—just minutes from Easton—Lakeside at Trappe offers an amenity-rich lifestyle. Residents enjoy a pool, bathhouse with fitness room, ping pong, cornhole, playground, sports courts, and a dedicated Bark Park, with exciting future lakeside amenities to come. With easy access to Easton, Cambridge, and the surrounding Chesapeake Bay region, this community blends convenience, recreation, and value. Ask about builder incentive options

4 Beds ⋅ 4 Baths

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!! Don’t miss this incredible opportunity—3 Car Garage! 4 bedrooms, 3.5 baths, offering exceptional space and value for today’s lifestyle. Backing to trees for added privacy and a serene view, this home delivers both comfort and setting. The bright sunroom off the kitchen creates the perfect gathering space, while the kitchen itself shines with a farmhouse sink, white cabinetry, quartz countertops, and a gourmet stainless steel appliance package with a hood. Luxury vinyl plank flooring spans the main level. Upstairs, enjoy the convenience of a second-level laundry room with a utility sink. Located in Trappe, MD—just minutes from Easton—Lakeside at Trappe offers an amenity-rich lifestyle. Residents enjoy a pool, bathhouse with fitness room, ping pong, cornhole, playground, sports courts, and a dedicated Bark Park, with exciting future lakeside amenities to come. With easy access to Easton, Cambridge, and the surrounding Chesapeake Bay region, this community blends convenience, recreation, and value. Ask about builder incentive options

1953 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

$669,900

ABSOLUTELY A MUST-SEE!...This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foyer with its impressive 8 ft wood entry door and into the designer gourmet kitchen, featuring a large island, sleek quartz countertops, stainless steel appliances, propane cooktop, wall oven, and gorgeous lighting. The kitchen also offers under cabinet lighting and a custom pantry with a cubby area, perfect for keeping shoes, coats, jackets, and hats organized. The kitchen and dining area seamlessly adjoin the inviting living room, featuring a cozy fireplace and elegant 8-foot French doors that flood the space with natural light while creating a seamless connection to the outdoors. It’s the perfect setting for both everyday living and entertaining. The first floor also offers a bedroom with a full bathroom, currently being used as an office, providing flexibility for work from home needs. Upstairs you'll be impressed by the abundance of space. The spacious primary suite features a beautiful en-suite bathroom with a double vanity and tiled walk-in shower. Two additional bedrooms and a full bathroom provide plenty of room for your family/or guests. And there's more!!! A large family/game room provides the perfect bonus space for movie nights, game days, hobbies, or simply spreading out and relaxing. Outside, enjoy both a welcoming front porch and spacious back porch, along with a paver patio area perfect for a fire pit, outdoor dining or just relaxing. The lush landscaping adds to the home's curb appeal, while a row of cypress trees lines the property and will provide beautiful privacy as they mature. Additional highlights include high ceilings, upscale lighting, LVP flooring and ceramic tile flooring. The home features an abundance of storage area throughout for organization. For ultimate convenience, the second floor laundry room comes fully equipped with a handy folding table and a hanging clothes rack. Rounding out this impressive property is an attached side entry garage that enhances the home's exterior profile. This home has it all, space, style, upgrades, privacy, and an incredible layout. Just a few miles from picturesque historic Chestertown and Centreville, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! Don't delay!! Come see this beauty before someone else gets the opportunity to call it home. You will want this one to be yours!

4 Beds ⋅ 3 Baths

ABSOLUTELY A MUST-SEE!...This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foyer with its impressive 8 ft wood entry door and into the designer gourmet kitchen, featuring a large island, sleek quartz countertops, stainless steel appliances, propane cooktop, wall oven, and gorgeous lighting. The kitchen also offers under cabinet lighting and a custom pantry with a cubby area, perfect for keeping shoes, coats, jackets, and hats organized. The kitchen and dining area seamlessly adjoin the inviting living room, featuring a cozy fireplace and elegant 8-foot French doors that flood the space with natural light while creating a seamless connection to the outdoors. It’s the perfect setting for both everyday living and entertaining. The first floor also offers a bedroom with a full bathroom, currently being used as an office, providing flexibility for work from home needs. Upstairs you'll be impressed by the abundance of space. The spacious primary suite features a beautiful en-suite bathroom with a double vanity and tiled walk-in shower. Two additional bedrooms and a full bathroom provide plenty of room for your family/or guests. And there's more!!! A large family/game room provides the perfect bonus space for movie nights, game days, hobbies, or simply spreading out and relaxing. Outside, enjoy both a welcoming front porch and spacious back porch, along with a paver patio area perfect for a fire pit, outdoor dining or just relaxing. The lush landscaping adds to the home's curb appeal, while a row of cypress trees lines the property and will provide beautiful privacy as they mature. Additional highlights include high ceilings, upscale lighting, LVP flooring and ceramic tile flooring. The home features an abundance of storage area throughout for organization. For ultimate convenience, the second floor laundry room comes fully equipped with a handy folding table and a hanging clothes rack. Rounding out this impressive property is an attached side entry garage that enhances the home's exterior profile. This home has it all, space, style, upgrades, privacy, and an incredible layout. Just a few miles from picturesque historic Chestertown and Centreville, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! Don't delay!! Come see this beauty before someone else gets the opportunity to call it home. You will want this one to be yours!

458 Eagle Manor Dr, Church Hill

Listing courtesy of Clark & Co Realty, LLC. Contact:

$549,000

Favorable rates. Flawless timing. Finalize your move before the holidays. This move-in-ready home offers the perfect opportunity to lock in a lower rate and settle in before the holidays! Why wait to build? This beautifully finished 2026 home is complete, move-in ready, and situated on a spacious one-acre lot in Church Hill’s desirable Condor Manor community. Offering 2,016 square feet, 4 bedrooms, 2.5 baths, and a two-car garage, this home combines modern finishes, energy-efficient construction, and the outdoor space today’s buyers are looking for. Step inside to a bright, open first floor featuring durable luxury vinyl plank flooring and plenty of room for everyday living and entertaining. The kitchen is the heart of the home with granite countertops, stainless steel appliances, and 42” American Woodmark cabinetry. Two generous living areas and a dining space provide flexibility for entertaining, relaxing, a home office, or play space, with peaceful views of the backyard. Upstairs, upgraded wall-to-wall carpeting creates a comfortable retreat. The spacious primary suite features a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide plenty of room for family, guests, hobbies, or office space. Built with efficiency and convenience in mind, the home features enhanced insulation, Low-E windows and doors, energy-efficient mechanical systems, and a conditioned crawl space. The two-car garage is pre-wired for electric vehicle charging, and the large driveway provides ample additional parking. Enjoy your morning coffee on the covered front porch or entertain on the 12’ x 16’ rear deck overlooking the expansive backyard. With a full acre, there’s room for pets, gardening, recreation, outdoor entertaining, and future projects—or simply enjoy having more privacy and breathing room. Located just outside the town of Church Hill with convenient access to Routes 213 and 301, Condor Manor offers a peaceful Eastern Shore setting while keeping commuting routes within easy reach. Newly built. One full acre. Four bedrooms. Move-in ready. And now offered at a great new price. Schedule your private showing and see the value this home has to offer. This community consists of 26 homes/lots . NOTE: At the time of listing, the calculated taxes reflect the assessment on the property and do not yet include the newly built home/improvements. Buyers should verify future tax assessments.

4 Beds ⋅ 3 Baths

Favorable rates. Flawless timing. Finalize your move before the holidays. This move-in-ready home offers the perfect opportunity to lock in a lower rate and settle in before the holidays! Why wait to build? This beautifully finished 2026 home is complete, move-in ready, and situated on a spacious one-acre lot in Church Hill’s desirable Condor Manor community. Offering 2,016 square feet, 4 bedrooms, 2.5 baths, and a two-car garage, this home combines modern finishes, energy-efficient construction, and the outdoor space today’s buyers are looking for. Step inside to a bright, open first floor featuring durable luxury vinyl plank flooring and plenty of room for everyday living and entertaining. The kitchen is the heart of the home with granite countertops, stainless steel appliances, and 42” American Woodmark cabinetry. Two generous living areas and a dining space provide flexibility for entertaining, relaxing, a home office, or play space, with peaceful views of the backyard. Upstairs, upgraded wall-to-wall carpeting creates a comfortable retreat. The spacious primary suite features a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide plenty of room for family, guests, hobbies, or office space. Built with efficiency and convenience in mind, the home features enhanced insulation, Low-E windows and doors, energy-efficient mechanical systems, and a conditioned crawl space. The two-car garage is pre-wired for electric vehicle charging, and the large driveway provides ample additional parking. Enjoy your morning coffee on the covered front porch or entertain on the 12’ x 16’ rear deck overlooking the expansive backyard. With a full acre, there’s room for pets, gardening, recreation, outdoor entertaining, and future projects—or simply enjoy having more privacy and breathing room. Located just outside the town of Church Hill with convenient access to Routes 213 and 301, Condor Manor offers a peaceful Eastern Shore setting while keeping commuting routes within easy reach. Newly built. One full acre. Four bedrooms. Move-in ready. And now offered at a great new price. Schedule your private showing and see the value this home has to offer. This community consists of 26 homes/lots . NOTE: At the time of listing, the calculated taxes reflect the assessment on the property and do not yet include the newly built home/improvements. Buyers should verify future tax assessments.

334 Eagle Manor Dr, Church Hill

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

$525,000

Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years old. From the moment you step inside, you’ll appreciate the home’s attention to detail, including soaring ceilings and an elegant tray ceiling in the dining room. The warm and welcoming family room is centered around a gas fireplace, creating the perfect setting for relaxing evenings or gathering with family and friends. Designed with convenient main-level living in mind, the spacious primary suite is located on the first floor and is enhanced by a beautiful tray ceiling. The private primary bath features a walk-in shower and soaking tub, creating your own relaxing retreat at the end of the day. At the heart of the home is a spectacular kitchen featuring granite countertops and beautiful 42-inch maple cabinetry, offering plenty of workspace and storage for everyday living and entertaining. The additional sunroom may quickly become one of your favorite places in the home. Enjoy your morning coffee while looking out over the stone patio and surrounding trees, where wild turkeys and deer may be among your morning visitors. Need a little extra space? A room above the garage with both heat and air conditioning provides wonderful flexibility. Create a home office, hobby or craft room, exercise space, media room, or comfortable retreat—the possibilities are yours. Whether you’re ready to simplify your lifestyle, enjoy the benefits of a welcoming 55+ community, or simply find a beautiful home where you can relax and enjoy everything the Eastern Shore has to offer, 29796 Lyons Drive is more than a home—it’s a destination.

3 Beds ⋅ 3 Baths

Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years old. From the moment you step inside, you’ll appreciate the home’s attention to detail, including soaring ceilings and an elegant tray ceiling in the dining room. The warm and welcoming family room is centered around a gas fireplace, creating the perfect setting for relaxing evenings or gathering with family and friends. Designed with convenient main-level living in mind, the spacious primary suite is located on the first floor and is enhanced by a beautiful tray ceiling. The private primary bath features a walk-in shower and soaking tub, creating your own relaxing retreat at the end of the day. At the heart of the home is a spectacular kitchen featuring granite countertops and beautiful 42-inch maple cabinetry, offering plenty of workspace and storage for everyday living and entertaining. The additional sunroom may quickly become one of your favorite places in the home. Enjoy your morning coffee while looking out over the stone patio and surrounding trees, where wild turkeys and deer may be among your morning visitors. Need a little extra space? A room above the garage with both heat and air conditioning provides wonderful flexibility. Create a home office, hobby or craft room, exercise space, media room, or comfortable retreat—the possibilities are yours. Whether you’re ready to simplify your lifestyle, enjoy the benefits of a welcoming 55+ community, or simply find a beautiful home where you can relax and enjoy everything the Eastern Shore has to offer, 29796 Lyons Drive is more than a home—it’s a destination.

29796 Lyons Dr, Easton

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

$1,150,000

NEW PRICE! A recent appraisal supports the list price, so you can buy with confidence. Don’t miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there’s plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design — clean lines, an inviting flow, and character you can’t replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house — it’s a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home. One small thing: with two bedrooms total, “the additional bedrooms” in the third paragraph reads as plural. You might change it to “the second bedroom, office, and full baths” so it matches the bedroom count.

3 Beds ⋅ 3 Baths

NEW PRICE! A recent appraisal supports the list price, so you can buy with confidence. Don’t miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there’s plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design — clean lines, an inviting flow, and character you can’t replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house — it’s a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home. One small thing: with two bedrooms total, “the additional bedrooms” in the third paragraph reads as plural. You might change it to “the second bedroom, office, and full baths” so it matches the bedroom count.

408 Butlers Lndg, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

$599,000

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities.

3 Beds ⋅ 3 Baths

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities.

6280 Bellevue Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$359,000

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

2 Beds ⋅ 2 Baths

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

101 S College Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$2,769,900

Finally Finished***From March 2026 until August 2026 the home went through its final finishing touch stages. There have been recent upgrades including water and electric to the pier.***Designed by YSA Homes and Simply Wesley Interior Design of Annapolis, this extraordinary brand-new modern coastal farmhouse style smart-home offers over 6,148 square feet of thoughtfully designed living space, where every tile throughout the home was handpicked and expertly curated using top-of-the-line luxury selections. The kitchen is outfitted with premium, top-tier appliances including Wolf, creating a seamless blend of elevated craftsmanship, timeless design, and modern functionality at every turn. The property is permitted for a pool to be built. This stunning residence features five oversized bedrooms, each with their own expansive en suite bathrooms, and three of the five have waterfront bay views. Totals include six full bathrooms, two half bathrooms, five gigantic bedrooms, 2 car oversized attached garage with rear entry door. An owner’s suite on the main level (with huge custom closet) provides everyday convenience, while the second level includes an additional owner’s suite with a massive custom walk-in closet, ideal for multi-generational living or extended guest stays. Upon entering the home, you are welcomed into an open-concept main level where the kitchen flows seamlessly into the dining and living areas, creating an ideal setting for entertaining and everyday living. The living room is anchored by a striking wireless water vapor fireplace, offering modern ambiance without heat or emissions. A main-level half bath adds convenience, while the primary suite features a spa-inspired oversized bathroom with a soaking tub, a large European-style walk-in shower, and exquisite designer finishes throughout. The second level impresses with a spacious great room, complete with a wet bar and an additional half bath, opening to a large upper-level deck designed for optimal water views and entertaining. Four generously sized en suite bedrooms are located on this level, two of which showcase stunning water views through oversized windows, filling the space with natural light. The lower level offers exceptional flexibility, featuring a walk-out basement with exterior sliding doors, a full bathroom, a dedicated laundry room, and ample space for a game room, den, home gym, or additional living areas. Ask the listing agent about available improvement and build-out options for the basement. Outdoor living continues on the main-level patio, with the option to expand or customize to suit your vision. ***The home features a brand new pier and a brand new well. Ask agent about shutter options. Washer- dryers on 2nd level and in basement (2 sets). Ask agent for 6th bedroom option to be included. Located on sought-after Kent Island, this home offers access to a true Chesapeake Bay lifestyle just approximately 20 minutes from historic downtown Annapolis. Nearby waterfront parks, marinas, beaches, and miles of scenic walking and biking trails along the Cross Island Trail. Golf enthusiasts will appreciate proximity to Blue Heron Golf Course with membership options available, as well as the nationally recognized Queenstown Harbor Golf Links featuring two championship courses. Residents can easily enjoy all that downtown Annapolis has to offer, including boutique shopping, waterfront dining, sailing culture, festivals, and the charm of the historic district and U.S. Naval Academy. Just minutes away, **Queenstown Premium Outlets. Kent Island is also home to waterfront dining, local crab houses, and Love Point Vineyards, while Terrapin Nature Park and Matapeake Beach offer stunning Chesapeake Bay views. Conveniently positioned for commuting to Baltimore and Washington, D.C., this location blends coastal living with everyday accessibility. This is not just a home, this is a coastal lifestyle.

5 Beds ⋅ 8 Baths

Finally Finished***From March 2026 until August 2026 the home went through its final finishing touch stages. There have been recent upgrades including water and electric to the pier.***Designed by YSA Homes and Simply Wesley Interior Design of Annapolis, this extraordinary brand-new modern coastal farmhouse style smart-home offers over 6,148 square feet of thoughtfully designed living space, where every tile throughout the home was handpicked and expertly curated using top-of-the-line luxury selections. The kitchen is outfitted with premium, top-tier appliances including Wolf, creating a seamless blend of elevated craftsmanship, timeless design, and modern functionality at every turn. The property is permitted for a pool to be built. This stunning residence features five oversized bedrooms, each with their own expansive en suite bathrooms, and three of the five have waterfront bay views. Totals include six full bathrooms, two half bathrooms, five gigantic bedrooms, 2 car oversized attached garage with rear entry door. An owner’s suite on the main level (with huge custom closet) provides everyday convenience, while the second level includes an additional owner’s suite with a massive custom walk-in closet, ideal for multi-generational living or extended guest stays. Upon entering the home, you are welcomed into an open-concept main level where the kitchen flows seamlessly into the dining and living areas, creating an ideal setting for entertaining and everyday living. The living room is anchored by a striking wireless water vapor fireplace, offering modern ambiance without heat or emissions. A main-level half bath adds convenience, while the primary suite features a spa-inspired oversized bathroom with a soaking tub, a large European-style walk-in shower, and exquisite designer finishes throughout. The second level impresses with a spacious great room, complete with a wet bar and an additional half bath, opening to a large upper-level deck designed for optimal water views and entertaining. Four generously sized en suite bedrooms are located on this level, two of which showcase stunning water views through oversized windows, filling the space with natural light. The lower level offers exceptional flexibility, featuring a walk-out basement with exterior sliding doors, a full bathroom, a dedicated laundry room, and ample space for a game room, den, home gym, or additional living areas. Ask the listing agent about available improvement and build-out options for the basement. Outdoor living continues on the main-level patio, with the option to expand or customize to suit your vision. ***The home features a brand new pier and a brand new well. Ask agent about shutter options. Washer- dryers on 2nd level and in basement (2 sets). Ask agent for 6th bedroom option to be included. Located on sought-after Kent Island, this home offers access to a true Chesapeake Bay lifestyle just approximately 20 minutes from historic downtown Annapolis. Nearby waterfront parks, marinas, beaches, and miles of scenic walking and biking trails along the Cross Island Trail. Golf enthusiasts will appreciate proximity to Blue Heron Golf Course with membership options available, as well as the nationally recognized Queenstown Harbor Golf Links featuring two championship courses. Residents can easily enjoy all that downtown Annapolis has to offer, including boutique shopping, waterfront dining, sailing culture, festivals, and the charm of the historic district and U.S. Naval Academy. Just minutes away, **Queenstown Premium Outlets. Kent Island is also home to waterfront dining, local crab houses, and Love Point Vineyards, while Terrapin Nature Park and Matapeake Beach offer stunning Chesapeake Bay views. Conveniently positioned for commuting to Baltimore and Washington, D.C., this location blends coastal living with everyday accessibility. This is not just a home, this is a coastal lifestyle.

414 Bay Dr, Stevensville

Listing courtesy of Cummings & Co. Realtors. Contact:

$1,675,000

105 Night Heron is a substantially expanded and renovated home offering more than 4400 square feet of finished living space plus an additional 850 square feet of finished, conditioned, multi-purpose garage space. The property features expansive water views and numerous high end finishes including custom Omega cabinetry, granite and black walnut countertops, extensive built-ins, premium Miele, Viking and Sharp appliances, hardwood and limestone flooring, Kohler fixtures, a custom coffered bar-room ceiling, a 500-bottle wine storage room, and extensive recess lighting. The main floor boasts a dream kitchen with breakfast area and fireplace and a formal dining room off the foyer with designer lighting that is included in the sale. A bar and billiards room has custom cabinetry, a pool table and seating area with fireplace, and views of Eastern Bay. Also on this floor is a formal living room with fireplace, a home office with Bay views, and a large mud-laundry room with adjoining powder room. The large primary suite has 3 closets in the bedroom area as well as a walk in closet and dressing room with custom cabinetry and natural light. The large primary bath has custom cabinetry with lots of storage, a separate tub and shower, dual sinks, limestone floors and a separate water closet. The second floor loft opens to two more bedrooms and a shared bath. One of the bedrooms leads to a veranda with stone fireplace and sweeping views of Eastern Bay. Appliances include a Miele refrigerator and freezer, Viking gas range, dishwasher, microwave, warming drawer, beverage and wine coolers, washer and dryer, garage refrigerator and beverage station and a Napoleon outdoor grill. Televisions and sound bars located in the bar area, club room, second floor loft and kitchen are included in the sale. The garage includes two Lift Master garage door openers, two SunPro motorized screens and RaceDeck flooring. Cove Creek Club is situated on 334 acres of large home sites with beautiful landscaping and views of Eastern Bay. Amenities include a USGA rated golf course, a private marina with direct access to Eastern Bay, boat ramp and storage yard, a private sandy beach, tennis, basketball and bocce ball courts, a club house and event facility, pro shop, walking and biking trails, and an exercise facility. It is conveniently located to Annapolis, Baltimore, Washington DC and Philadelphia.

3 Beds ⋅ 4 Baths

105 Night Heron is a substantially expanded and renovated home offering more than 4400 square feet of finished living space plus an additional 850 square feet of finished, conditioned, multi-purpose garage space. The property features expansive water views and numerous high end finishes including custom Omega cabinetry, granite and black walnut countertops, extensive built-ins, premium Miele, Viking and Sharp appliances, hardwood and limestone flooring, Kohler fixtures, a custom coffered bar-room ceiling, a 500-bottle wine storage room, and extensive recess lighting. The main floor boasts a dream kitchen with breakfast area and fireplace and a formal dining room off the foyer with designer lighting that is included in the sale. A bar and billiards room has custom cabinetry, a pool table and seating area with fireplace, and views of Eastern Bay. Also on this floor is a formal living room with fireplace, a home office with Bay views, and a large mud-laundry room with adjoining powder room. The large primary suite has 3 closets in the bedroom area as well as a walk in closet and dressing room with custom cabinetry and natural light. The large primary bath has custom cabinetry with lots of storage, a separate tub and shower, dual sinks, limestone floors and a separate water closet. The second floor loft opens to two more bedrooms and a shared bath. One of the bedrooms leads to a veranda with stone fireplace and sweeping views of Eastern Bay. Appliances include a Miele refrigerator and freezer, Viking gas range, dishwasher, microwave, warming drawer, beverage and wine coolers, washer and dryer, garage refrigerator and beverage station and a Napoleon outdoor grill. Televisions and sound bars located in the bar area, club room, second floor loft and kitchen are included in the sale. The garage includes two Lift Master garage door openers, two SunPro motorized screens and RaceDeck flooring. Cove Creek Club is situated on 334 acres of large home sites with beautiful landscaping and views of Eastern Bay. Amenities include a USGA rated golf course, a private marina with direct access to Eastern Bay, boat ramp and storage yard, a private sandy beach, tennis, basketball and bocce ball courts, a club house and event facility, pro shop, walking and biking trails, and an exercise facility. It is conveniently located to Annapolis, Baltimore, Washington DC and Philadelphia.

105 Night Heron Ct, Stevensville

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

$400,000

Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. NOTE: Manufactured home with skirting-- without a foundation- so it may impact financing approvals. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

3 Beds ⋅ 2 Baths

Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. NOTE: Manufactured home with skirting-- without a foundation- so it may impact financing approvals. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

405 Rings End Rd, Millington

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$281,000

Significant price correction! Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. No property address has yet been assigned to the 9,381 sq ft lot; the 3,097 parcel is designated as 620 Cannon Street. Buyer to verify zoning, permitted uses, building requirements, and utility availability. Each lot is listed separately in separate listings.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

$349,997

Welcome to 25133 Smithville Rd.! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining. Step outside to enjoy the spacious, level backyard with fencing for added privacy. There is plenty of room for entertaining, family gatherings, kids, pets, outdoor activities, and more—all while enjoying your own private outdoor space. With its spacious layout, convenient main-level primary suite, and private backyard, this home offers a wonderful opportunity to make it your own. Come see all that 25133 Smithville Rd. has to offer and make this home yours!

4 Beds ⋅ 3 Baths

Welcome to 25133 Smithville Rd.! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining. Step outside to enjoy the spacious, level backyard with fencing for added privacy. There is plenty of room for entertaining, family gatherings, kids, pets, outdoor activities, and more—all while enjoying your own private outdoor space. With its spacious layout, convenient main-level primary suite, and private backyard, this home offers a wonderful opportunity to make it your own. Come see all that 25133 Smithville Rd. has to offer and make this home yours!

25133 Smithville Rd, Worton

Listing courtesy of Allfirst Realty, Inc.. Contact:

$196,000

Major price reduction! Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. The adjacent lot at the corner of Cannon and Lynchburg is also available for purchase. No property address has yet been assigned to this lot. Buyer to verify zoning, permitted uses, building requirements, and utility availability.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

$899,000

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

5 Beds ⋅ 3 Baths

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

14 Fairway Is, Grasonville

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

$339,000

Discover the potential of this 4-bedroom, 2-full-bath home in the desirable Rio Vista community of St. Michaels! Offering a spacious two-level layout, this property presents a fantastic opportunity for buyers looking to make a home their own or investors searching for their next project. Inside, you'll find hardwood floors, a separate dining room, a galley kitchen, and comfortable living spaces with plenty of possibilities. The flexible floor plan provides room to reimagine, update, and create a space that fits your needs. Step outside to enjoy a generously sized yard with plenty of space for entertaining, gardening, or simply relaxing outdoors. A storage shed adds convenience and additional storage. Located in the established Rio Vista community, residents enjoy access to wonderful neighborhood amenities, including a community boat ramp, kayak launch, and marina, making it easy to embrace the Eastern Shore lifestyle. Enjoy all the charm, shopping, and dining of historic St. Michaels while benefiting from a location outside the town limits. This home is ready for some TLC, but the opportunity is undeniable! Whether you're an investor, renovator, or buyer with a vision, this property offers the chance to create something special in a sought-after waterfront community. Bring your ideas and discover the possibilities!

4 Beds ⋅ 2 Baths

Discover the potential of this 4-bedroom, 2-full-bath home in the desirable Rio Vista community of St. Michaels! Offering a spacious two-level layout, this property presents a fantastic opportunity for buyers looking to make a home their own or investors searching for their next project. Inside, you'll find hardwood floors, a separate dining room, a galley kitchen, and comfortable living spaces with plenty of possibilities. The flexible floor plan provides room to reimagine, update, and create a space that fits your needs. Step outside to enjoy a generously sized yard with plenty of space for entertaining, gardening, or simply relaxing outdoors. A storage shed adds convenience and additional storage. Located in the established Rio Vista community, residents enjoy access to wonderful neighborhood amenities, including a community boat ramp, kayak launch, and marina, making it easy to embrace the Eastern Shore lifestyle. Enjoy all the charm, shopping, and dining of historic St. Michaels while benefiting from a location outside the town limits. This home is ready for some TLC, but the opportunity is undeniable! Whether you're an investor, renovator, or buyer with a vision, this property offers the chance to create something special in a sought-after waterfront community. Bring your ideas and discover the possibilities!

214 Madison Ave, Saint Michaels

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$279,999

Back on the market! Price Reduction! Amazing remodel! Home is a 3-bedroom, 1 bath home in Millington, MD with easy access to Rte. 301 for any daily commute! There is an additional room that could be used as a 4th bedroom or an office. Home sits on a half-acre of property with a huge side yard for any new buildings or storage needs. Home has well and septic so no quarterly water and sewer bills! Updates include a completely new kitchen with stainless steel appliances and quartz countertops, new wood style LPV flooring, new HVAC, metal roof, front porch, back deck, new ceiling fans, recessed lights, new water treatment system, newer septic, newer well pump and newer bladder tank. This place shines beautifully! Build equity! Pay a mortgage for less than you can pay rent! Make your appointment today and see all that this home has to offer. Call Lori for your private tour!

3 Beds ⋅ 1 Baths

Back on the market! Price Reduction! Amazing remodel! Home is a 3-bedroom, 1 bath home in Millington, MD with easy access to Rte. 301 for any daily commute! There is an additional room that could be used as a 4th bedroom or an office. Home sits on a half-acre of property with a huge side yard for any new buildings or storage needs. Home has well and septic so no quarterly water and sewer bills! Updates include a completely new kitchen with stainless steel appliances and quartz countertops, new wood style LPV flooring, new HVAC, metal roof, front porch, back deck, new ceiling fans, recessed lights, new water treatment system, newer septic, newer well pump and newer bladder tank. This place shines beautifully! Build equity! Pay a mortgage for less than you can pay rent! Make your appointment today and see all that this home has to offer. Call Lori for your private tour!

210 Groff Rd, Millington

Listing courtesy of RE/MAX Chesapeake. Contact:

$730,000

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

3 Beds ⋅ 3 Baths

Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

216 Birch Run Rd, Chestertown

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

$1,500,000

Rare opportunity to acquire both the real estate and established business of Blue Heron Oyster House & Inn, a highly popular neighborhood restaurant in the heart of Rock Hall. Opened in June 2022, Blue Heron has quickly developed a loyal following among residents and visitors, with waits for tables common during peak dining hours. The building was completely renovated inside and out in early 2022 and offers more than 4,000 square feet across two levels. The main level features an immaculate commercial kitchen, indoor and outdoor cold storage, dining and bar areas, and extensive indoor/outdoor service space. Furniture, fixtures and equipment are less than five years old, with a complete inventory available upon request. Indoor seating accommodates approximately 55 guests at tables plus 24 bar seats. Outdoor dining expands capacity with approximately 42 table seats and 26 additional seats at the tiki bar, bringing total seasonal seating capacity to approximately 147. More than 1,000 square feet on the second floor includes three inn rooms that are not currently being rented, providing an opportunity for a new owner to establish an additional lodging component and year-round revenue stream. An additional office and storage areas are also located upstairs. The property offers 24 on-site parking spaces, with additional parking currently available along Coleman Road and Route 20. Located just two blocks from Ferry Park Beach and within walking and biking distance of several Rock Hall marinas, Blue Heron is well positioned to serve both the local community and visitors to this popular Chesapeake Bay town. The restaurant currently operates approximately 27 hours per week, Wednesday through Sunday, and traditionally closes for a few weeks during the winter. Sale includes the real estate and operating business. Additional business information and FF&E inventory are available to qualified buyers upon execution of an NDA.

20658 Wilkins Ave, Rock Hall

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

$535,000

Price reduced! 1-Acre Centreville Home with Detached Pole Barn & Major System Upgrades This move-in-ready 1-acre Centreville property paired with a large detached pole barn delivers complete peace of mind with major mechanical upgrades, including a 3-year-old heat pump, 1-year-old water heater, replacement windows (2018), and a high-end water treatment and softener system. Designed for low-maintenance living and effortless entertaining, the home features a screened-in porch, custom paver patio, partially fenced yard, updated lighting, ceiling fans, and four new storm doors. Enjoy space, privacy, and no HOA minutes from Downtown Centreville and US-301.

3 Beds ⋅ 2 Baths

Price reduced! 1-Acre Centreville Home with Detached Pole Barn & Major System Upgrades This move-in-ready 1-acre Centreville property paired with a large detached pole barn delivers complete peace of mind with major mechanical upgrades, including a 3-year-old heat pump, 1-year-old water heater, replacement windows (2018), and a high-end water treatment and softener system. Designed for low-maintenance living and effortless entertaining, the home features a screened-in porch, custom paver patio, partially fenced yard, updated lighting, ceiling fans, and four new storm doors. Enjoy space, privacy, and no HOA minutes from Downtown Centreville and US-301.

639 Poplar School Rd, Centreville

Listing courtesy of Compass. Contact:

$359,900

Open House, Sunday, 11/15 from 1-4PM * Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all -Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

3 Beds ⋅ 3 Baths

Open House, Sunday, 11/15 from 1-4PM * Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all -Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

108 Blenny Ln, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$85,000

Price correction! Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available. Buyer to confirm with the Town of Chestertown allowable uses and the use of the previous water/sewer allocation.

620 Cannon St, Chestertown

Listing courtesy of Taylor Properties. Contact:

How much is your home worth?

How much is your home worth?