easternshoremdfineproperties.com Search Results

Welcome to 10 Ericsson Ave #33 in the waterfront community of Betterton, where everyday living feels like a permanent getaway. Nestled within the peaceful enclave of Rigbie Bluff, this inviting, updated, and move-in ready condo offers a rare blend of tranquility, charm, and scenic beauty. This well-appointed two-bedroom, two-bath residence is conveniently located on the ground level, making move-in effortless and everyday living easily accessible. Inside, you’ll find a comfortable layout designed for relaxation after a day spent enjoying the water and surrounding nature. Wake up each morning to sweeping views of the Chesapeake Bay, where sailboats drift by and maritime traffic creates an ever-changing coastal backdrop. Whether you're enjoying your morning coffee or unwinding at sunset, the water views and natural surroundings provide a constant sense of calm. For boating enthusiasts, the deeded private boat slip with hoist makes it simple to hop on your boat and cruise the bay at a moment’s notice. Spend your days exploring the shoreline, fishing, or enjoying endless waterfront adventures just steps from your door. Rigbie Bluff is known for its relaxed, small-town atmosphere—perfect for those seeking a slower pace without sacrificing connection. Enjoy time by the community pool, where you can unwind, soak up the sun, and let your worries drift away. This remarkable condo is ready for you to experience all that Betterton and the Chesapeake Bay have to offer—whether as a full-time residence or the perfect weekend escape. Come discover a place where serenity, community, and coastal living come together effortlessly.

10 Ericsson Ave Unit 33, Betterton

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

Selling Office: ExecuHome Realty.

$315,000

Beach day… or boat day.......maybe pool day? 🌊🚤 Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury. This condo is perfectly positioned with breathtaking views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the Sassafras River. Step inside this inviting 2-bedroom, 2 full bath end-unit condo, where additional windows invite in natural light and frame the surrounding water views. The open-concept living, dining, and kitchen areas create an effortless flow—ideal for both everyday living and entertaining. Slide open the doors and step onto your expansive private balcony, where panoramic water views and vibrant sunsets set the tone. Let the rhythm of the waves and the distant call of bald eagles become the soundtrack to your mornings and evenings—an experience that simply can’t be replicated. 🌅🦅 For the boating enthusiast, this is truly exceptional—a private HOA pier, your own boat slip, AND a boat lift all convey with the sale. From kayaking and paddleboarding to waterskiing and cruising the Bay, everything you love about waterfront living is just steps away—from your balcony to the beach in under 60 seconds. 🚤 The community also offers access to a private saltwater pool, creating a rare combination of beach, boating, and poolside living all in one location. 🏊‍♀️ Thoughtfully updated, this home features new flooring throughout, updated kitchen appliances with a stylish backsplash, and a NEW HVAC system (Fall 2025)—offering comfort and peace of mind for the next owner. Ohhh and did I mention a huge storage room right below your unit for all your water toys & more? Betterton is known for its welcoming charm, scenic shoreline, and seasonal events. Enjoy summer days filled with beachside relaxation, waterfront activities, holiday fireworks, and beloved traditions like Betterton Appreciation Days—all just moments from your door. 💫 Priced at $315,000, this is a standout opportunity to secure a waterfront lifestyle just in time to enjoy the full summer season. 📅 Open House: Sunday, April 12th | 11:00 AM – 1:00 PM A rare offering combining location, lifestyle, and value—schedule your showing before it’s gone.

Beach day… or boat day.......maybe pool day? 🌊🚤 Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury. This condo is perfectly positioned with breathtaking views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the Sassafras River. Step inside this inviting 2-bedroom, 2 full bath end-unit condo, where additional windows invite in natural light and frame the surrounding water views. The open-concept living, dining, and kitchen areas create an effortless flow—ideal for both everyday living and entertaining. Slide open the doors and step onto your expansive private balcony, where panoramic water views and vibrant sunsets set the tone. Let the rhythm of the waves and the distant call of bald eagles become the soundtrack to your mornings and evenings—an experience that simply can’t be replicated. 🌅🦅 For the boating enthusiast, this is truly exceptional—a private HOA pier, your own boat slip, AND a boat lift all convey with the sale. From kayaking and paddleboarding to waterskiing and cruising the Bay, everything you love about waterfront living is just steps away—from your balcony to the beach in under 60 seconds. 🚤 The community also offers access to a private saltwater pool, creating a rare combination of beach, boating, and poolside living all in one location. 🏊‍♀️ Thoughtfully updated, this home features new flooring throughout, updated kitchen appliances with a stylish backsplash, and a NEW HVAC system (Fall 2025)—offering comfort and peace of mind for the next owner. Ohhh and did I mention a huge storage room right below your unit for all your water toys & more? Betterton is known for its welcoming charm, scenic shoreline, and seasonal events. Enjoy summer days filled with beachside relaxation, waterfront activities, holiday fireworks, and beloved traditions like Betterton Appreciation Days—all just moments from your door. 💫 Priced at $315,000, this is a standout opportunity to secure a waterfront lifestyle just in time to enjoy the full summer season. 📅 Open House: Sunday, April 12th | 11:00 AM – 1:00 PM A rare offering combining location, lifestyle, and value—schedule your showing before it’s gone.

10 Ericsson Ave Unit 37, Betterton

Listing courtesy of Remax Vision. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$300,000

Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy. The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step outside and enjoy the fully fenced backyard, complete with a storage shed, cozy patio area, and fire pit area, making it perfect for relaxing or entertaining. Dont wait to see this one!

Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy. The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step outside and enjoy the fully fenced backyard, complete with a storage shed, cozy patio area, and fire pit area, making it perfect for relaxing or entertaining. Dont wait to see this one!

7464 Shortall St, Chestertown

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

Selling Office: Benson & Mangold, LLC.

$300,000

The one you’ve been waiting for! This extensively updated 3 bedroom, 2 full bath ranch boasts 1,376 square feet of open living space and a roomy 2 car garage. The property sits at the end of a quiet street and lies adjacent to farm land and a pond with a seasonal view. Enjoy serene privacy from your spacious 20 x 16 deck! The home is beautifully remodeled and updated with a new stone driveway and landscaping, HVAC, hot water heater, waterproof LVP flooring, fresh paint, and new lighting and fixtures throughout. The custom kitchen features a large walk in pantry, new stainless steel appliance package, high quality 36” soft close cabinetry, and gorgeous quartz countertops paired with a custom tile backsplash. The Primary bedroom is bright and spacious with a walk-in closet and Primary bath that impresses with a custom tiled walk-in shower. The 2nd and 3rd bedrooms are a generous size and offer easy access to a full bathroom with a tub/shower surround. This home is 10 minutes from Chestertown, 35 minutes from Middletown, DE, 12 minutes from Betterton Beach and offers quick access to numerous boat ramps and all the Chesapeake has to offer. A thoughtfully remodeled home boasting all of these features won’t last long!

The one you’ve been waiting for! This extensively updated 3 bedroom, 2 full bath ranch boasts 1,376 square feet of open living space and a roomy 2 car garage. The property sits at the end of a quiet street and lies adjacent to farm land and a pond with a seasonal view. Enjoy serene privacy from your spacious 20 x 16 deck! The home is beautifully remodeled and updated with a new stone driveway and landscaping, HVAC, hot water heater, waterproof LVP flooring, fresh paint, and new lighting and fixtures throughout. The custom kitchen features a large walk in pantry, new stainless steel appliance package, high quality 36” soft close cabinetry, and gorgeous quartz countertops paired with a custom tile backsplash. The Primary bedroom is bright and spacious with a walk-in closet and Primary bath that impresses with a custom tiled walk-in shower. The 2nd and 3rd bedrooms are a generous size and offer easy access to a full bathroom with a tub/shower surround. This home is 10 minutes from Chestertown, 35 minutes from Middletown, DE, 12 minutes from Betterton Beach and offers quick access to numerous boat ramps and all the Chesapeake has to offer. A thoughtfully remodeled home boasting all of these features won’t last long!

11054 Austin Ln, Worton

Listing courtesy of RE/MAX Chesapeake. Contact:

Selling Office: LPT Realty, LLC.

$300,000

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private ensuite bathroom. Surrounded by the beauty of Maryland's Eastern Shore, this property is ideal for those who appreciate outdoor living, with countless nearby opportunities for hunting, fishing, crabbing, boating, and exploring nature. Enjoy the charm, history, shops, dining, and waterfront attractions that make Chestertown such a sought-after destination while still embracing the peace and privacy of a rural setting. Mortgage savings may be available for buyers of this listing.

4 Beds ⋅ 2 Baths

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town amenities. Enjoy easy one-level living with a functional layout and gorgeous hardwood floors that add warmth and character throughout the home. The beautiful white kitchen features stainless steel appliances, including a gas range and microwave range hood, creating a bright and inviting space for everyday living and entertaining. The home offers four main-level bedrooms, including a comfortable owner's suite with a private ensuite bathroom. Surrounded by the beauty of Maryland's Eastern Shore, this property is ideal for those who appreciate outdoor living, with countless nearby opportunities for hunting, fishing, crabbing, boating, and exploring nature. Enjoy the charm, history, shops, dining, and waterfront attractions that make Chestertown such a sought-after destination while still embracing the peace and privacy of a rural setting. Mortgage savings may be available for buyers of this listing.

304 Hadaway Dr, Chestertown

Listing courtesy of Redfin Corporation. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$299,000

This beautifully updated home in Rock Hall offers a blend of classic charm and modern improvements. The open living area features refinished original fir wood floors and flows into an updated kitchen with gas range, dishwasher, refrigerator and ample workspace that is ideal for everyday cooking or entertaining. The main level includes a bedroom and full bath, while the second-floor owner’s suite offers a spacious bedroom, full bath, and flexible office or sitting area. This home has been thoughtfully updated over the past 5 years including newer vinyl windows throughout, newer HVAC, brand-new roof, tankless water heater and gutter guards. A separate laundry room with exterior entrance is ideal for gardeners or pets. Large outbuilding with second-floor storage offers great space for hobbies or a workshop. Sitting on over 3/4 of an acre and located less than a mile from the public boat launch and landing, this home is perfect for a weekend getaway, summer retreat or year-round living.

This beautifully updated home in Rock Hall offers a blend of classic charm and modern improvements. The open living area features refinished original fir wood floors and flows into an updated kitchen with gas range, dishwasher, refrigerator and ample workspace that is ideal for everyday cooking or entertaining. The main level includes a bedroom and full bath, while the second-floor owner’s suite offers a spacious bedroom, full bath, and flexible office or sitting area. This home has been thoughtfully updated over the past 5 years including newer vinyl windows throughout, newer HVAC, brand-new roof, tankless water heater and gutter guards. A separate laundry room with exterior entrance is ideal for gardeners or pets. Large outbuilding with second-floor storage offers great space for hobbies or a workshop. Sitting on over 3/4 of an acre and located less than a mile from the public boat launch and landing, this home is perfect for a weekend getaway, summer retreat or year-round living.

5188 Skinners Neck Rd, Rock Hall

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$296,500

This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.

2 Beds ⋅ 3 Baths

This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.

108 Oak Leaf Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$293,000

Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining. The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is inviting. This home offers three comfortable bedrooms and two full bathrooms, along with modern upgrades including ENERGY STAR windows and an updated washer and dryer. Situated on a generous 0.41-acre lot, the property provides plenty of outdoor space for relaxing, gardening, or entertaining. The surrounding community is known for its welcoming atmosphere, with nearby parks and recreational areas that support an active lifestyle. Conveniently located just a short drive from Downtown Chestertown, you’ll enjoy easy access to local shops, dining, and waterfront charm. Move-in ready and beautifully updated, this home combines comfort, functionality, and location — an excellent opportunity to enjoy Eastern Shore living at its best.

Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining. The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is inviting. This home offers three comfortable bedrooms and two full bathrooms, along with modern upgrades including ENERGY STAR windows and an updated washer and dryer. Situated on a generous 0.41-acre lot, the property provides plenty of outdoor space for relaxing, gardening, or entertaining. The surrounding community is known for its welcoming atmosphere, with nearby parks and recreational areas that support an active lifestyle. Conveniently located just a short drive from Downtown Chestertown, you’ll enjoy easy access to local shops, dining, and waterfront charm. Move-in ready and beautifully updated, this home combines comfort, functionality, and location — an excellent opportunity to enjoy Eastern Shore living at its best.

301 Lincoln Dr, Chestertown

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

Selling Office: Foraker Realty Co..

$290,000

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$290,000

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨

2 Beds ⋅ 3 Baths

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨

522 High St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: CR Realty.

$290,000

Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space that can be used as a home office, gym, recreation room, or additional living area. This level also offers walk-out access to the rear, adding even more functionality. Upstairs on the main level, you’ll find a spacious living room with beautiful wood flooring, perfect for relaxing or entertaining. A convenient half bath is located nearby for guests. The kitchen offers both functionality and style, featuring upgraded granite countertops, tile flooring, a pantry closet, and an island with an electric stove and downdraft ventilation system. The adjoining dining area provides a comfortable space for meals and gatherings. Just off the kitchen, step out onto a nice rear deck with a pergola that backs to trees—an ideal spot to unwind or enjoy outdoor dining. The third level features two generously sized bedrooms, including a primary suite with an attached bathroom complete with a walk-in shower. A full hall bath serves the additional bedroom, and a hall closet houses a front-load stackable washer and dryer for added convenience. Additional closets provide ample storage space. As an end unit, this home enjoys extra privacy and natural light. Located in an HOA community with very little maintenance required, this home offers easy living in a peaceful and convenient setting.

2 Beds ⋅ 3 Baths

Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space that can be used as a home office, gym, recreation room, or additional living area. This level also offers walk-out access to the rear, adding even more functionality. Upstairs on the main level, you’ll find a spacious living room with beautiful wood flooring, perfect for relaxing or entertaining. A convenient half bath is located nearby for guests. The kitchen offers both functionality and style, featuring upgraded granite countertops, tile flooring, a pantry closet, and an island with an electric stove and downdraft ventilation system. The adjoining dining area provides a comfortable space for meals and gatherings. Just off the kitchen, step out onto a nice rear deck with a pergola that backs to trees—an ideal spot to unwind or enjoy outdoor dining. The third level features two generously sized bedrooms, including a primary suite with an attached bathroom complete with a walk-in shower. A full hall bath serves the additional bedroom, and a hall closet houses a front-load stackable washer and dryer for added convenience. Additional closets provide ample storage space. As an end unit, this home enjoys extra privacy and natural light. Located in an HOA community with very little maintenance required, this home offers easy living in a peaceful and convenient setting.

115 Acorn Dr, Chestertown

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

Selling Office: Doug Ashley Realtors, LLC.

$277,000

This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living area, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new LVP flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. Underneath the carpet reveals the same wide plank flooring as downstairs. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.To top it all off, both the home and the garage are in the process of getting brand new roofs! Hurry, this one won't last!

This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living area, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new LVP flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. Underneath the carpet reveals the same wide plank flooring as downstairs. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.To top it all off, both the home and the garage are in the process of getting brand new roofs! Hurry, this one won't last!

6022 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: LPT Realty, LLC.

$275,000

Sellers are offering $5,000 in closing cost help for an acceptable offer! Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite bath, while the main living level features a seamless flow from kitchen to dining and family room—ideal for everyday living and entertaining. Upstairs, the primary bedroom boasts vaulted ceilings and a private balcony, alongside an additional bedroom and full bath. The garage provides ideal storage for water toys, fishing gear, or a golf cart. Whether you’re looking for a full-time residence or an easy weekend escape, this home delivers the best of Rock Hall living.

3 Beds ⋅ 3 Baths

Sellers are offering $5,000 in closing cost help for an acceptable offer! Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite bath, while the main living level features a seamless flow from kitchen to dining and family room—ideal for everyday living and entertaining. Upstairs, the primary bedroom boasts vaulted ceilings and a private balcony, alongside an additional bedroom and full bath. The garage provides ideal storage for water toys, fishing gear, or a golf cart. Whether you’re looking for a full-time residence or an easy weekend escape, this home delivers the best of Rock Hall living.

21103 Striper Run, Rock Hall

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

Selling Office: Benson & Mangold, LLC.

$270,000

Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include new windows (2020), a brand-new fenced yard, a new deck perfect for outdoor enjoyment, and bathroom updates featuring a Bath Fitter system with a lifetime warranty. Additional improvements include new gutters with LeafFilter protection and a new washer and dryer, offering peace of mind and low-maintenance living for years to come. Enjoy the ease of single-level living in a revitalized small-town community while still being conveniently located near Route 301 for quick commuting access. Millington’s local shops, dining, parks, and nearby waterways make this an ideal home base for those seeking both charm and convenience. Pride of ownership shines throughout, making this home an excellent opportunity for first-time buyers, downsizers, or anyone looking for a well-cared-for property in a welcoming Eastern Shore community.

Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include new windows (2020), a brand-new fenced yard, a new deck perfect for outdoor enjoyment, and bathroom updates featuring a Bath Fitter system with a lifetime warranty. Additional improvements include new gutters with LeafFilter protection and a new washer and dryer, offering peace of mind and low-maintenance living for years to come. Enjoy the ease of single-level living in a revitalized small-town community while still being conveniently located near Route 301 for quick commuting access. Millington’s local shops, dining, parks, and nearby waterways make this an ideal home base for those seeking both charm and convenience. Pride of ownership shines throughout, making this home an excellent opportunity for first-time buyers, downsizers, or anyone looking for a well-cared-for property in a welcoming Eastern Shore community.

423 Cypress St, Millington

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$269,000

Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby! Owner had a pre home inspection for your convenance! The home is good to go! For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready. The layout offers comfort and privacy with the primary suite tucked away on one side of the home, while the three additional bedrooms are located on the opposite side, perfect for maybe or a home office setup. The home is connected to public water and sewer, and also offers fiber internet, giving you modern convenience in a laid-back coastal setting. Step outside and enjoy the freedom that comes with no restrictions—bring your boat, RV, or water toys, and if you’ve been dreaming of building a pole barn or workshop, you can do that here too. Located just minutes from creeks, rivers, and the Chesapeake Bay, this home places you right in the heart of one of the Eastern Shore’s most beloved boating towns. Rock Hall may only have one traffic light, but it’s full of life—with marinas, waterfront restaurants, coffee shops, boutiques, ice cream stops, and a quaint downtown. The town hosts events throughout the year, creating that true small-town vibe where everyone knows your name—or soon will. If you’ve been searching for a fun, beachy lifestyle with small-town charm, modern updates, and room for your boats and hobbies, this home delivers. Rock Hall — where nice people live. *some photos have been enhanced with virtual staging*

4 Beds ⋅ 2 Baths

Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby! Owner had a pre home inspection for your convenance! The home is good to go! For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready. The layout offers comfort and privacy with the primary suite tucked away on one side of the home, while the three additional bedrooms are located on the opposite side, perfect for maybe or a home office setup. The home is connected to public water and sewer, and also offers fiber internet, giving you modern convenience in a laid-back coastal setting. Step outside and enjoy the freedom that comes with no restrictions—bring your boat, RV, or water toys, and if you’ve been dreaming of building a pole barn or workshop, you can do that here too. Located just minutes from creeks, rivers, and the Chesapeake Bay, this home places you right in the heart of one of the Eastern Shore’s most beloved boating towns. Rock Hall may only have one traffic light, but it’s full of life—with marinas, waterfront restaurants, coffee shops, boutiques, ice cream stops, and a quaint downtown. The town hosts events throughout the year, creating that true small-town vibe where everyone knows your name—or soon will. If you’ve been searching for a fun, beachy lifestyle with small-town charm, modern updates, and room for your boats and hobbies, this home delivers. Rock Hall — where nice people live. *some photos have been enhanced with virtual staging*

6374 Rock Hall Rd, Rock Hall

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

Selling Office: Crown Homes Real Estate.

$264,900

Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless-steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Ask about Special Financing Offers and how to get $6,300 or more in closing help from the builders' preferred lender!

Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless-steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Ask about Special Financing Offers and how to get $6,300 or more in closing help from the builders' preferred lender!

109 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Real Broker, LLC.

$262,000

Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 1 additional bedroom adds options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $5,000 that can be paid off with installments, annually over 5-10 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 1 additional bedroom adds options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $5,000 that can be paid off with installments, annually over 5-10 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

10971 Bottom Rd, Worton

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

Selling Office: RE/MAX Chesapeake.

$260,000

Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is - below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction. Conveniently located with an easy commute to Route 301 and just around the corner from the newer YMCA. Enjoy all that Chestertown has to offer, from its charming small-town atmosphere and wonderful restaurants to artistic venues, community events, and Washington College. A must-see for buyers looking for a newer home, excellent condition, and exceptional value in a great location!

3 Beds ⋅ 3 Baths

Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is - below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction. Conveniently located with an easy commute to Route 301 and just around the corner from the newer YMCA. Enjoy all that Chestertown has to offer, from its charming small-town atmosphere and wonderful restaurants to artistic venues, community events, and Washington College. A must-see for buyers looking for a newer home, excellent condition, and exceptional value in a great location!

249 Island Lark Way, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$259,900

Welcome to 25003 Heather Ln! This well maintained 3 bedroom, 2 full bath home offers the ease of first floor living in a quiet neighborhood. Inside, you'll find an open concept layout with high ceilings that create a bright, spacious feel, along with modern finishes throughout. Outside, the huge yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Move in ready and conveniently located, this home is one you won't want to miss. Schedule your showing today!

Welcome to 25003 Heather Ln! This well maintained 3 bedroom, 2 full bath home offers the ease of first floor living in a quiet neighborhood. Inside, you'll find an open concept layout with high ceilings that create a bright, spacious feel, along with modern finishes throughout. Outside, the huge yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Move in ready and conveniently located, this home is one you won't want to miss. Schedule your showing today!

25003 Heather Ln, Worton

Listing courtesy of Crown Homes Real Estate. Contact:

Selling Office: The Land Group.

$259,900

Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Up to $7,500 in closing help available on select models when using builders partner lender and title company.

Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations. Up to $7,500 in closing help available on select models when using builders partner lender and title company.

107 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$258,000

Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields.

4 Beds ⋅ 2 Baths

Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields.

6445 Edesville Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$249,000

Sought after location in College Heights. Short walk to downtown Chestertown and Parks. This cozy rancher is a diamond in the rough and is ready for new owners! located on a safe and quiet street, with public water and sewer with municipal pickups. Don't miss your opportunity to live in a great location! Being sold as is and priced accordingly.

Sought after location in College Heights. Short walk to downtown Chestertown and Parks. This cozy rancher is a diamond in the rough and is ready for new owners! located on a safe and quiet street, with public water and sewer with municipal pickups. Don't miss your opportunity to live in a great location! Being sold as is and priced accordingly.

112 Elm St, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Bayside Realty.

$245,000

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

107 Conley Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Cummings & Co. Realtors.

$244,000

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

2 Beds ⋅ 1 Baths

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

21217 Texas Ave, Chestertown

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: Cross Street Realtors LLC.

$240,000

Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Don’t miss the opportunity to make this beautifully upgraded Cape Cod your new home.

Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Don’t miss the opportunity to make this beautifully upgraded Cape Cod your new home.

11060 Plum Dr, Worton

Listing courtesy of Patterson-Schwartz-Newark. Contact:

Selling Office: Empower Real Estate, LLC.

$238,000

***Offer deadline tomorrow Sunday, October 18 at 2pm*** Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher offers 1,008 square feet of easy, low maintenance one-level living on a .37 acre lot with plenty of room to spread out. As you walk into the front door, you enjoy a lovely living space with an open floor plan leading into the kitchen. Down the hall, you have 3 bedrooms and a newly renovated bathroom. This home has been meticulously maintained and updated from top to bottom over the last 4 years including a new roof, new HVAC, new flooring throughout, a water conditioning system, all new stainless steel appliances, a new storm door, and more. There’s so much to enjoy nearby. Launch your boat from the community ramp at Worton Creek Marina and spend the day on the water. Then end it with dinner at a local favorite, The View at Worton Creek. This home is located just a short drive from Chestertown, Rock Hall and the Safe Harbor Marina. Whether you’re buying your very first home or looking for a wonderful rental to add to your portfolio, this one is ready to welcome you. Come see it for yourself!

***Offer deadline tomorrow Sunday, October 18 at 2pm*** Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher offers 1,008 square feet of easy, low maintenance one-level living on a .37 acre lot with plenty of room to spread out. As you walk into the front door, you enjoy a lovely living space with an open floor plan leading into the kitchen. Down the hall, you have 3 bedrooms and a newly renovated bathroom. This home has been meticulously maintained and updated from top to bottom over the last 4 years including a new roof, new HVAC, new flooring throughout, a water conditioning system, all new stainless steel appliances, a new storm door, and more. There’s so much to enjoy nearby. Launch your boat from the community ramp at Worton Creek Marina and spend the day on the water. Then end it with dinner at a local favorite, The View at Worton Creek. This home is located just a short drive from Chestertown, Rock Hall and the Safe Harbor Marina. Whether you’re buying your very first home or looking for a wonderful rental to add to your portfolio, this one is ready to welcome you. Come see it for yourself!

10484 Cogar Rd, Chestertown

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$235,000

Older house that sets on 4.58 acres of land. Very quiet with views of the open acreage behind the house. A few sheds on the property and located near the end of the street. Walking distance to the public water.

Older house that sets on 4.58 acres of land. Very quiet with views of the open acreage behind the house. A few sheds on the property and located near the end of the street. Walking distance to the public water.

21263 Allens Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

$222,000

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights.A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights.A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

202 Pine St, Chestertown

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

Selling Office: Taylor Properties.

$220,500

Adorable small 2 Bedroom, 1 Bath, home located in the eventful town of Rock Hall. A great starter home or 2nd home while you're visiting Rock Hall on your boat. An affordable, easily maintained home within walking or biking distance to restaurants, shopping and marinas. Cute front porch to sit and enjoy your days and evenings.

2 Beds ⋅ 1 Baths

Adorable small 2 Bedroom, 1 Bath, home located in the eventful town of Rock Hall. A great starter home or 2nd home while you're visiting Rock Hall on your boat. An affordable, easily maintained home within walking or biking distance to restaurants, shopping and marinas. Cute front porch to sit and enjoy your days and evenings.

5548 Boundary Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Advantage Realty.

$215,000

Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything. Most homes in this price range make you choose: updated systems or a great location. This one delivers both. Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the Eastern Shore's most walkable town right outside your front door — without the noise or traffic. The home has been completely overhauled from the outside in. New metal roof, gutters, downspouts, vinyl siding, and windows protect your investment from the elements before you ever step inside. Inside, a new HVAC system, updated 200-amp electrical panel, new hot water heater, and fully replaced water main and plumbing mean zero deferred maintenance — just move in and live. Refinished hardwood floors and new vinyl flooring run throughout open, light-filled spaces. The updated bathroom features a new vanity, and the laundry room comes equipped with a brand-new washer and dryer. The kitchen opens directly into the dining area and flows into the family room — a layout that makes everyday living easy and entertaining effortless. Start your mornings on the enclosed porch. Host friends on a generous corner lot with room to breathe. Park conveniently on the private gravel pad with direct kitchen access. This is what move-in ready actually looks like. Schedule your tour today.