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INVESTORS!! THIS COULD BE YOUR NEXT PROJECT!! Estate Sale – Peaceful Tranquility on the Eastern Shore There’s something special about living near the water—the smell of the bay, the calm in the air, and the sound of birds all around you. This brick rancher in the desirable Marling Farms community is right in the center of it all. With views of Crab Alley Creek and located within the Chester River watershed, the setting offers the peaceful lifestyle so many seek on the Eastern Shore. While the home needs a little TLC, it’s graciously waiting for its next homeowner to bring their vision to life. The property is being sold AS-IS, and no repairs will be made—BUT- it’s the perfect opportunity to add your own special touches. The home does feature a newer roof.... update to suit your taste-- Highlights include a welcoming front porch, attached two-car garage, and a driveway that accommodates additional parking. Inside, you'll find a spacious living room with a fireplace (ambiance for a snow-fall) and walls of windows that allow natural light to pour in while showcasing the surrounding beauty. .. and a view of the Crab Alley Bay is just across the road-- The home also offers an entrance foyer, an eat-in kitchen, and a four-season sunroom overlooking open green space—perfect for relaxing or gathering with family and friends. Situated on a little over a half-acre lot, the backyard offers a blank canvas to create your own outdoor oasis. The home includes one full and one half bathroom, two bedrooms, and a versatile breezeway bonus room currently set up as a club room with a pool table. This flexible space could easily be converted into additional living space or a bedroom— There is also a laundry closet and ample storage throughout. Marling Farms is a water-oriented community surrounded by natural beauty, offering three beach areas with playgrounds and covered picnic spaces. You don’t have to be a crabber or fisherman—but those hobbies certainly fit right in here! Enjoy nature walks, fishing, or relaxing at the community waterfront. Located just minutes from waterfront restaurants, shopping, and everyday conveniences on Kent Island-- Its the home you’ve always wanted in a water community—You just have to get here

1905 Bayside Dr, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: RE/MAX Leading Edge.

$285,000

Opportunity on Kent Island! This charming 3 -bedroom, 1-bath home offers 1300 square feet of comfortable living space on a quiet street. Bring your vision and creativity--the property needs renovation and is being sold "as is", but has great potential to become a charming island retreat or year-round residence. Enjoy the peaceful setting while still being just minutes from the Bay Bridge, local restaurants, and waterfront parks. Whether you're looking for your first home, a weekend retreat, or a downsizing opportunity, this property offers the perfect blend of comfort, location, and value. This is a great chance to invest in the Kent Island lifestyle--don't miss out on this affordable opportunity to make it your own.

Opportunity on Kent Island! This charming 3 -bedroom, 1-bath home offers 1300 square feet of comfortable living space on a quiet street. Bring your vision and creativity--the property needs renovation and is being sold "as is", but has great potential to become a charming island retreat or year-round residence. Enjoy the peaceful setting while still being just minutes from the Bay Bridge, local restaurants, and waterfront parks. Whether you're looking for your first home, a weekend retreat, or a downsizing opportunity, this property offers the perfect blend of comfort, location, and value. This is a great chance to invest in the Kent Island lifestyle--don't miss out on this affordable opportunity to make it your own.

957 Cloverfields Dr, Stevensville

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Keller Williams Flagship.

$285,000

REDUCED!! REDUCED!! This affordable 3 Bedroom 1 full bath located in Centreville has solid hardwood floors throughout. Needs updating but functional and everything works. Located within walking distance to Downtown Centreville which offers, Acme Supermarket, great Dining and Farmers market. Great investor potential or rental.

REDUCED!! REDUCED!! This affordable 3 Bedroom 1 full bath located in Centreville has solid hardwood floors throughout. Needs updating but functional and everything works. Located within walking distance to Downtown Centreville which offers, Acme Supermarket, great Dining and Farmers market. Great investor potential or rental.

125 Price St, Centreville

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity. Enjoy relaxing or entertaining on the rear deck, then take advantage of Dundee Harbor's water privileges on Piney Creek, including a private community pier for fishing, kayaking, paddleboarding, crabbing, or simply enjoying the waterfront. Just minutes from Kent Narrows, you'll love the waterfront restaurants, marinas, boat ramps, tiki bars, live entertainment, and Chesapeake Bay lifestyle. Conveniently located near shopping, everyday conveniences, and Route 50, this home offers an easy commute while delivering the relaxed Eastern Shore lifestyle buyers are looking for. Whether you're searching for an investment property, primary residence, or weekend retreat, this Estate Sale is an opportunity you won't want to miss. Schedule your showing today!

3 Beds ⋅ 3 Baths

Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity. Enjoy relaxing or entertaining on the rear deck, then take advantage of Dundee Harbor's water privileges on Piney Creek, including a private community pier for fishing, kayaking, paddleboarding, crabbing, or simply enjoying the waterfront. Just minutes from Kent Narrows, you'll love the waterfront restaurants, marinas, boat ramps, tiki bars, live entertainment, and Chesapeake Bay lifestyle. Conveniently located near shopping, everyday conveniences, and Route 50, this home offers an easy commute while delivering the relaxed Eastern Shore lifestyle buyers are looking for. Whether you're searching for an investment property, primary residence, or weekend retreat, this Estate Sale is an opportunity you won't want to miss. Schedule your showing today!

1025 Dundee Ct, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Douglas Realty LLC.

Eastern Shore charm in the heart of Grasonville! This adorable cottage offers easy one-level living and features a thoughtfully designed addition that creates an expansive gathering space perfect for entertaining family and friends. Accessibility is enhanced with a convenient ramp, making everyday living comfortable and practical. Numerous improvements have been completed over the years, including an energy-efficient mini-split heating and cooling system. Move-in ready and full of character, this home presents an excellent opportunity for buyers seeking affordability, convenience, and Eastern Shore living. Being sold as-is, with plenty of potential for a handy homeowner to add their own finishing touches and build additional equity.

2 Beds ⋅ 1 Baths

Eastern Shore charm in the heart of Grasonville! This adorable cottage offers easy one-level living and features a thoughtfully designed addition that creates an expansive gathering space perfect for entertaining family and friends. Accessibility is enhanced with a convenient ramp, making everyday living comfortable and practical. Numerous improvements have been completed over the years, including an energy-efficient mini-split heating and cooling system. Move-in ready and full of character, this home presents an excellent opportunity for buyers seeking affordability, convenience, and Eastern Shore living. Being sold as-is, with plenty of potential for a handy homeowner to add their own finishing touches and build additional equity.

4003 Main St, Grasonville

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

Selling Office: Keller Williams Realty.

"Why rent when you can own?" or are you looking for a weekend home? This condo is has so many options at an affordable price. Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Also, owning the upper level gives you the security if you are a lock and leave weekender. 2nd floor condos feature vaulted ceilings that are unavailable on the main level. Soaring vaulted ceilings, open floor, beautiful hardwood floors, gourmet Kitchen offers all brand new appliances including refrigerator, dishwasher, stove with glass top, microwave and garbage disposal. The beautiful living area features a gas fireplace for those chilly days coming soon and the dining area is perfect for entertaining and flows from the kitchen, dining to the balcony. This condo also includes a new efficient hot water heater and stackable full size washer and dryer. Owner has meticulously maintained this home. The spacious primary suite offers a peaceful retreat with a generous bedroom, walk-in closet and a private ensuite bath. A second bedroom provides exceptional flexibility as a guest room, home office, or space for family and grandchildren. Another full bath is located near the second bedroom. Beyond the home, enjoy an exceptional lifestyle with access to community amenities including a clubhouse, swimming pool, pickleball courts, and fitness center. A marina is within walking distance, making it easy to enjoy boating and waterfront activities. Bayside is a friendly pet community with many paths for dog walking. The cross trail is just steps from your condo. The condominium association handles exterior maintenance and community upkeep, allowing you more time to enjoy the things you love. Ideally situated near fine dining, shopping, and cultural attractions, this location also offers outstanding accessibility—within easy reach of three international airports—making travel convenient whether for business, family visits, or leisure. This is the perfect opportunity to enjoy a low-maintenance lifestyle without sacrificing comfort, convenience, or amenities. "Elevated living, exceptional amenities, and a carefree lifestyle—all in one remarkable home."

"Why rent when you can own?" or are you looking for a weekend home? This condo is has so many options at an affordable price. Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Also, owning the upper level gives you the security if you are a lock and leave weekender. 2nd floor condos feature vaulted ceilings that are unavailable on the main level. Soaring vaulted ceilings, open floor, beautiful hardwood floors, gourmet Kitchen offers all brand new appliances including refrigerator, dishwasher, stove with glass top, microwave and garbage disposal. The beautiful living area features a gas fireplace for those chilly days coming soon and the dining area is perfect for entertaining and flows from the kitchen, dining to the balcony. This condo also includes a new efficient hot water heater and stackable full size washer and dryer. Owner has meticulously maintained this home. The spacious primary suite offers a peaceful retreat with a generous bedroom, walk-in closet and a private ensuite bath. A second bedroom provides exceptional flexibility as a guest room, home office, or space for family and grandchildren. Another full bath is located near the second bedroom. Beyond the home, enjoy an exceptional lifestyle with access to community amenities including a clubhouse, swimming pool, pickleball courts, and fitness center. A marina is within walking distance, making it easy to enjoy boating and waterfront activities. Bayside is a friendly pet community with many paths for dog walking. The cross trail is just steps from your condo. The condominium association handles exterior maintenance and community upkeep, allowing you more time to enjoy the things you love. Ideally situated near fine dining, shopping, and cultural attractions, this location also offers outstanding accessibility—within easy reach of three international airports—making travel convenient whether for business, family visits, or leisure. This is the perfect opportunity to enjoy a low-maintenance lifestyle without sacrificing comfort, convenience, or amenities. "Elevated living, exceptional amenities, and a carefree lifestyle—all in one remarkable home."

114 Merganser Ct, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

Welcome to easy, coastal living in Bayside on Kent Island. This beautifully updated first-floor condo offers the perfect blend of comfort, convenience, and the lifestyle everyone loves about Kent Island. Step inside to a fresh, move-in-ready interior featuring brand-new hardwood floors in the entryway and kitchen, new appliances, and plush new carpet in both bedrooms. The entire condo has been freshly painted, creating a bright and inviting space throughout. The layout includes 2 spacious bedrooms and 2 full bathrooms, highlighted by a large primary suite with a generous walk-in closet and private bath. Living in Bayside means enjoying more than just a home, it’s a lifestyle. The community features scenic ponds, walking paths, a clubhouse, pool, fitness center, and tennis courts, all set within beautifully maintained grounds surrounding Castle Marina. Even better, you’re just steps from a walking trail that connects directly to the Kent Island Cross Island Trail, offering miles of scenic paths perfect for walking, biking, and enjoying the waterfront lifestyle. If you’ve been searching for low-maintenance living with resort-style amenities and access to one of Kent Island’s most loved trails, this condo is the perfect place to call home.

Welcome to easy, coastal living in Bayside on Kent Island. This beautifully updated first-floor condo offers the perfect blend of comfort, convenience, and the lifestyle everyone loves about Kent Island. Step inside to a fresh, move-in-ready interior featuring brand-new hardwood floors in the entryway and kitchen, new appliances, and plush new carpet in both bedrooms. The entire condo has been freshly painted, creating a bright and inviting space throughout. The layout includes 2 spacious bedrooms and 2 full bathrooms, highlighted by a large primary suite with a generous walk-in closet and private bath. Living in Bayside means enjoying more than just a home, it’s a lifestyle. The community features scenic ponds, walking paths, a clubhouse, pool, fitness center, and tennis courts, all set within beautifully maintained grounds surrounding Castle Marina. Even better, you’re just steps from a walking trail that connects directly to the Kent Island Cross Island Trail, offering miles of scenic paths perfect for walking, biking, and enjoying the waterfront lifestyle. If you’ve been searching for low-maintenance living with resort-style amenities and access to one of Kent Island’s most loved trails, this condo is the perfect place to call home.

106 Merganser Ct, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: EXP Realty, LLC.

Charming farmhouse located in the quaint town of Church Hill. This home offers over 1,400 square feet of living space, featuring three bedrooms, one bathroom, a kitchen, a living room, and a designated dining area. The property also includes a welcoming front porch and sits on a spacious .80-acre lot. A highlight of this property is the expansive detached garage/workshop, equipped with a utility sink, wood stove for the cold winter months and a full second floor, offering endless possibilities for a studio, home office, or extensive storage. The home is conveniently situated between Centreville and Chestertown with easy access to Route 213 and Route 301. Just minutes away from water sports at Rolphs Wharf and other local boat launches, and only 25 minutes from Middletown, Delaware, for tax-free shopping.

Charming farmhouse located in the quaint town of Church Hill. This home offers over 1,400 square feet of living space, featuring three bedrooms, one bathroom, a kitchen, a living room, and a designated dining area. The property also includes a welcoming front porch and sits on a spacious .80-acre lot. A highlight of this property is the expansive detached garage/workshop, equipped with a utility sink, wood stove for the cold winter months and a full second floor, offering endless possibilities for a studio, home office, or extensive storage. The home is conveniently situated between Centreville and Chestertown with easy access to Route 213 and Route 301. Just minutes away from water sports at Rolphs Wharf and other local boat launches, and only 25 minutes from Middletown, Delaware, for tax-free shopping.

111 Cemetery Ln, Church Hill

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

Selling Office: Rosendale Realty.

$278,500

There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with attached carport located in Chester Harbor. There is a full unfinished basement and a 3 car detached garage all situated on 2 parcels that include 5 lots. Chester harbor offers water access to Rosin Creek.

There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with attached carport located in Chester Harbor. There is a full unfinished basement and a 3 car detached garage all situated on 2 parcels that include 5 lots. Chester harbor offers water access to Rosin Creek.

107 Longfellow Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Lofgren-Sargent Real Estate.

$276,000

Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in closet and a brand-new custom spa-like shower in the en-suite bath. A second bedroom and full bath provide plenty of space for family, guests, or a home office. Updates within the past few years include laminate flooring in the living areas, hallway, and baths, fresh carpet in both bedrooms and the primary closet, a modern interior paint palette, plus a newer HVAC, refrigerator, and microwave for added comfort and peace of mind. Bayside residents enjoy resort-style amenities such as a pool, tennis courts, fitness center, and clubhouse with a large party room. The unaffiliated Queens Landing Marina—just steps away—keeps your boat close, while the scenic Kent Island Trail offers miles of walking, jogging, and biking. All of this adds to the relaxed, vacation-like lifestyle of Maryland’s beautiful Eastern Shore!

Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in closet and a brand-new custom spa-like shower in the en-suite bath. A second bedroom and full bath provide plenty of space for family, guests, or a home office. Updates within the past few years include laminate flooring in the living areas, hallway, and baths, fresh carpet in both bedrooms and the primary closet, a modern interior paint palette, plus a newer HVAC, refrigerator, and microwave for added comfort and peace of mind. Bayside residents enjoy resort-style amenities such as a pool, tennis courts, fitness center, and clubhouse with a large party room. The unaffiliated Queens Landing Marina—just steps away—keeps your boat close, while the scenic Kent Island Trail offers miles of walking, jogging, and biking. All of this adds to the relaxed, vacation-like lifestyle of Maryland’s beautiful Eastern Shore!

201 Golden Eye Ct, Chester

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

Selling Office: Unrepresented Buyer Office.

$275,000

Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. This one-bedroom one-bath condo offers approximately 724 square feet with an open floor plan and a geourgous view. Walk into a bright living area that flows seemlessly into the adjacent kitchen, creating an inviting and functional space for everyday living or entertaining. The kitchen has been updated with granite countertops, stainless steel appliances, upgraded cabinetry with self-closing drawers, and a clean, modern layout that maximizes both storage and workspace. Luxury vinyl plank flooring was added throughout, giving the home a cohesive and low-maintenance finish. The living room also features handmade, unique Venetian Stucco wall art straight from Italy that adds character and warmth to the space. The bedroom is located on the marina side and opens directly to a private, partially covered patio with full marina views, making it the ideal spot to enjoy morning coffee or unwind at sunset. The sunsets here are among the best in the community. Two outdoor storage closets are located off the patio, a rare and valuable feature for a one-bedroom unit. Lower condo fees help keep monthly expenses manageable, making this an excellent option for a primary residence, second home, or weekend getaway. For added peace of mind, the seller is offering a one-year home warranty to the buyer.The building roof was replaced in 2020 with 30-year architectural shingles. Queens Landing is known for its Spanish-style architecture and resort-style amenities, including a waterfront heated pool, fitness center, tennis and pickleball courts, clubhouse, and walking paths along the Chester River and marina. Boat slips are available for rent or purchase, and residents enjoy the convenience of being able to walk to nearby restaurants. A rarely available marina front one bedroom offering water views, outdoor space, and affordability in one of Kent Island’s most established waterfront communities.

1 Beds ⋅ 1 Baths

Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. This one-bedroom one-bath condo offers approximately 724 square feet with an open floor plan and a geourgous view. Walk into a bright living area that flows seemlessly into the adjacent kitchen, creating an inviting and functional space for everyday living or entertaining. The kitchen has been updated with granite countertops, stainless steel appliances, upgraded cabinetry with self-closing drawers, and a clean, modern layout that maximizes both storage and workspace. Luxury vinyl plank flooring was added throughout, giving the home a cohesive and low-maintenance finish. The living room also features handmade, unique Venetian Stucco wall art straight from Italy that adds character and warmth to the space. The bedroom is located on the marina side and opens directly to a private, partially covered patio with full marina views, making it the ideal spot to enjoy morning coffee or unwind at sunset. The sunsets here are among the best in the community. Two outdoor storage closets are located off the patio, a rare and valuable feature for a one-bedroom unit. Lower condo fees help keep monthly expenses manageable, making this an excellent option for a primary residence, second home, or weekend getaway. For added peace of mind, the seller is offering a one-year home warranty to the buyer.The building roof was replaced in 2020 with 30-year architectural shingles. Queens Landing is known for its Spanish-style architecture and resort-style amenities, including a waterfront heated pool, fitness center, tennis and pickleball courts, clubhouse, and walking paths along the Chester River and marina. Boat slips are available for rent or purchase, and residents enjoy the convenience of being able to walk to nearby restaurants. A rarely available marina front one bedroom offering water views, outdoor space, and affordability in one of Kent Island’s most established waterfront communities.

6 Queen Victoria Way, Chester

Listing courtesy of Realty Navigator. Contact:

Selling Office: Redfin Corp.

$270,000

Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by recessed lighting. Step outside to a large deck overlooking a 15,000 square foot lot, perfect for relaxation and entertainment. This home features a playground and tennis court access for leisurely afternoons. With an attached garage, air conditioning, and in-building laundry, convenience is at your fingertips. Water enthusiasts will appreciate the nearby water access, while pickleball fans can enjoy a game on the community court. Situated in a friendly neighborhood, this home combines comfort with a variety of amenities to suit your lifestyle. Whether you’re cozying up by the fireplace or exploring the outdoors, 119 Darden Road is ready to welcome you home!

Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by recessed lighting. Step outside to a large deck overlooking a 15,000 square foot lot, perfect for relaxation and entertainment. This home features a playground and tennis court access for leisurely afternoons. With an attached garage, air conditioning, and in-building laundry, convenience is at your fingertips. Water enthusiasts will appreciate the nearby water access, while pickleball fans can enjoy a game on the community court. Situated in a friendly neighborhood, this home combines comfort with a variety of amenities to suit your lifestyle. Whether you’re cozying up by the fireplace or exploring the outdoors, 119 Darden Road is ready to welcome you home!

119 Darden Rd, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Clark & Co Realty, LLC.

$265,000

Beautifully maintained first-floor condominium featuring tranquil lake views and a bright, open floor plan designed for comfortable living and effortless entertaining. This inviting residence offers two generously sized bedrooms and two full bathrooms, providing both space and privacy. Sunlight fills the spacious living and dining areas, which open directly to a private patio overlooking the peaceful lake—an ideal setting for relaxing mornings or unwinding in the evening. Situated in the highly sought-after Bayside community, residents enjoy an exceptional array of amenities including scenic walking trails, a clubhouse with a party room, fitness center, swimming pool, and tennis courts. Conveniently located just minutes from shopping, dining, and major commuter routes, this home offers the perfect combination of comfort, convenience, and resort-style living.

Beautifully maintained first-floor condominium featuring tranquil lake views and a bright, open floor plan designed for comfortable living and effortless entertaining. This inviting residence offers two generously sized bedrooms and two full bathrooms, providing both space and privacy. Sunlight fills the spacious living and dining areas, which open directly to a private patio overlooking the peaceful lake—an ideal setting for relaxing mornings or unwinding in the evening. Situated in the highly sought-after Bayside community, residents enjoy an exceptional array of amenities including scenic walking trails, a clubhouse with a party room, fitness center, swimming pool, and tennis courts. Conveniently located just minutes from shopping, dining, and major commuter routes, this home offers the perfect combination of comfort, convenience, and resort-style living.

306 Teal T Unit C, Chester

Listing courtesy of Kelly and Co Realty, LLC. Contact:

Selling Office: Samson Properties.

$261,000

Sellers offering to pay capital contribution fee with acceptable offer. 55 and over community, this newly updated home features an inviting open floor plan, highlighted by luxurious vinyl plank and ceramic tile flooring, along with cozy carpeting in the primary bedroom. The galley kitchen, complete with upgraded countertops and built-ins, flows seamlessly into the dining and living areas, making it ideal for entertaining or quiet evenings at home. Enjoy the warmth of the gas fireplace, or step outside to your porch overlooking the beautifully maintained common areas. The property includes an attached garage with a paved driveway, ensuring easy access and ample parking. Residents benefit from a well-managed association that covers custodial services, exterior maintenance, and snow removal, allowing you to focus on enjoying life. The community offers lovely common grounds and a party room for gatherings. Located near local parks and excellent public services, this neighborhood fosters a vibrant lifestyle. With nearby towns like Chestertown and Centreville for shopping and restaurants and recreational facilities, you'll find everything you need just a short distance away. Experience the comfort of home in a community that values connection and convenience. Recent updates include; Finished 2nd floor with drywall, electric, lights & ceiling fans, paint and carpet. Installed new LVP flooring through most of 1st floor, installed foam insulation, new sump pump and dehumidifier in crawl space. Installed brand new REEM HVAC system. New washer/dryer. New water softener and reverse osmosis water filter. Completely new kitchen with cabinets, sink, quartz counter tops, disposal, gas stove/oven and under cabinet lighting. New insulated garage door with new opener and key pad entry. New ceiling fan in guest bedroom. New carpet in primary bedroom, new LVP flooring in primary bathroom, new light fixtures in primary bedroom and closets. Come see the 55+ community; The Pond at Church Hill. The community encircles a large, grassy, common area with a shaded pond at one end. This is an interior unit with 2 bedrooms/2 baths and newly finished 2nd floor that could be bedrooms, craft, or recreation room. Lots of possibilities.. The area also features 2 established community theatres!

Sellers offering to pay capital contribution fee with acceptable offer. 55 and over community, this newly updated home features an inviting open floor plan, highlighted by luxurious vinyl plank and ceramic tile flooring, along with cozy carpeting in the primary bedroom. The galley kitchen, complete with upgraded countertops and built-ins, flows seamlessly into the dining and living areas, making it ideal for entertaining or quiet evenings at home. Enjoy the warmth of the gas fireplace, or step outside to your porch overlooking the beautifully maintained common areas. The property includes an attached garage with a paved driveway, ensuring easy access and ample parking. Residents benefit from a well-managed association that covers custodial services, exterior maintenance, and snow removal, allowing you to focus on enjoying life. The community offers lovely common grounds and a party room for gatherings. Located near local parks and excellent public services, this neighborhood fosters a vibrant lifestyle. With nearby towns like Chestertown and Centreville for shopping and restaurants and recreational facilities, you'll find everything you need just a short distance away. Experience the comfort of home in a community that values connection and convenience. Recent updates include; Finished 2nd floor with drywall, electric, lights & ceiling fans, paint and carpet. Installed new LVP flooring through most of 1st floor, installed foam insulation, new sump pump and dehumidifier in crawl space. Installed brand new REEM HVAC system. New washer/dryer. New water softener and reverse osmosis water filter. Completely new kitchen with cabinets, sink, quartz counter tops, disposal, gas stove/oven and under cabinet lighting. New insulated garage door with new opener and key pad entry. New ceiling fan in guest bedroom. New carpet in primary bedroom, new LVP flooring in primary bathroom, new light fixtures in primary bedroom and closets. Come see the 55+ community; The Pond at Church Hill. The community encircles a large, grassy, common area with a shaded pond at one end. This is an interior unit with 2 bedrooms/2 baths and newly finished 2nd floor that could be bedrooms, craft, or recreation room. Lots of possibilities.. The area also features 2 established community theatres!

116 The Pond Way Unit 3C, Church Hill

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Douglas Realty LLC.

$260,000

Bay City - Opportunity Knocking for Investor! This 3 Bedroom 1.5 Bath rancher features a new roof 2020, Siding and Windows in 2017. The property is .42 of an acre with a nice backyard. The blacktop drive and one car garage are some other nice features. The home needs TLC and updating inside. The property is being sold in AS-IS condition, inspections are for information purposes only. Solar panels are owned and not leased.

Bay City - Opportunity Knocking for Investor! This 3 Bedroom 1.5 Bath rancher features a new roof 2020, Siding and Windows in 2017. The property is .42 of an acre with a nice backyard. The blacktop drive and one car garage are some other nice features. The home needs TLC and updating inside. The property is being sold in AS-IS condition, inspections are for information purposes only. Solar panels are owned and not leased.

303 Charl Ct, Stevensville

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

Selling Office: Five Star Real Estate.

$260,000

Chester River Charm: Your Gateway to Eastern Shore Living Completely Renovated Cottage with River Views & Endless Possibilities Discover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifully transformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristine Chester River. Whether you're seeking a weekend escape, investment opportunity, or year-round retreat, this property delivers on every front. The Perfect Package Step into a home that's been thoughtfully reimagined from top to bottom. The open, light-filled interior showcases luxury vinyl plank flooring, fresh paint throughout, and new lighting that creates an inviting atmosphere perfect for both relaxation and entertaining. The updated kitchen features brand-new stainless steel Frigidaire appliances, while plantation shutters and custom window treatments add elegant touches throughout. Every comfort has been considered with new Mitsubishi mini-split heating and cooling systems ensuring year-round efficiency, plus a cutting-edge Stiebel Eltron tankless water heater and energy-saving solar panels that make this home as smart as it is beautiful. Outdoor Living at Its Finest The real magic happens outside, where mature gardens tell the story of seasons past and future. Dogwoods and cherry blossoms frame slate walkways and stone borders, creating a landscape that's both sophisticated and naturally beautiful. The 12x16 treated lumber deck provides the perfect spot for morning coffee with river glimpses, while the 10x12 shed offers excellent storage with its updated siding and metal roof. Location Advantages Position yourself in one of Maryland's most coveted regions, where the Chester River's calm waters offer world-class fishing, kayaking, and boating just 2 miles away at Deep Landing Boat Ramp. Historic Chestertown brings year-round culture with festivals like the famous Tea Party celebration, Saturday farmers markets, vibrant arts scenes, and waterfront dining that draws visitors from across the region. The strategic location offers quick access to major corridors—25 minutes to the Chesapeake Bay Bridge opens up Baltimore and Washington DC markets, while Delaware's beaches and Middletown are equally close.

Chester River Charm: Your Gateway to Eastern Shore Living Completely Renovated Cottage with River Views & Endless Possibilities Discover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifully transformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristine Chester River. Whether you're seeking a weekend escape, investment opportunity, or year-round retreat, this property delivers on every front. The Perfect Package Step into a home that's been thoughtfully reimagined from top to bottom. The open, light-filled interior showcases luxury vinyl plank flooring, fresh paint throughout, and new lighting that creates an inviting atmosphere perfect for both relaxation and entertaining. The updated kitchen features brand-new stainless steel Frigidaire appliances, while plantation shutters and custom window treatments add elegant touches throughout. Every comfort has been considered with new Mitsubishi mini-split heating and cooling systems ensuring year-round efficiency, plus a cutting-edge Stiebel Eltron tankless water heater and energy-saving solar panels that make this home as smart as it is beautiful. Outdoor Living at Its Finest The real magic happens outside, where mature gardens tell the story of seasons past and future. Dogwoods and cherry blossoms frame slate walkways and stone borders, creating a landscape that's both sophisticated and naturally beautiful. The 12x16 treated lumber deck provides the perfect spot for morning coffee with river glimpses, while the 10x12 shed offers excellent storage with its updated siding and metal roof. Location Advantages Position yourself in one of Maryland's most coveted regions, where the Chester River's calm waters offer world-class fishing, kayaking, and boating just 2 miles away at Deep Landing Boat Ramp. Historic Chestertown brings year-round culture with festivals like the famous Tea Party celebration, Saturday farmers markets, vibrant arts scenes, and waterfront dining that draws visitors from across the region. The strategic location offers quick access to major corridors—25 minutes to the Chesapeake Bay Bridge opens up Baltimore and Washington DC markets, while Delaware's beaches and Middletown are equally close.

134 Char Nor Manor Blvd, Chestertown

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$258,000

Updated 2-Bedroom Condo with Garage in Water-Privileged Community – Immediate Occupancy! Don’t miss this beautifully renovated two-level condo featuring 2 bedrooms, 1.5 baths, and a one-car garage. Priced to sell! Thoughtfully updated over the past five years, this home offers newer carpet and luxury vinyl plank flooring, a remodeled kitchen and bathrooms, and a high-efficiency Bosch HVAC system. All major appliances—including kitchen appliances, oversized washer and dryer, and hot water heater—have been recently replaced. The main level features an open living room, galley-style kitchen, convenient half bath, and a versatile bonus room ideal for a dining area or home office. Sliding glass doors lead to a private rear deck with direct access to the parking area and spacious 21x10 garage. Upstairs, you’ll find two generously sized bedrooms and a full bath. Enjoy the benefits of a water-privileged community with access to a pool, pier, and boat docks. HOA fees cover fresh and wastewater, trash pickup, lawn care, shrub maintenance, roof and shingles, crawl space upkeep, exterior hose bib, pool, boat dock, fishing pier, and maintenance of common areas and entrance decking—providing low-maintenance living. Conveniently located for an easy commute to Rt. 50, Annapolis, and Easton, and within walking distance to restaurants and shopping.

Updated 2-Bedroom Condo with Garage in Water-Privileged Community – Immediate Occupancy! Don’t miss this beautifully renovated two-level condo featuring 2 bedrooms, 1.5 baths, and a one-car garage. Priced to sell! Thoughtfully updated over the past five years, this home offers newer carpet and luxury vinyl plank flooring, a remodeled kitchen and bathrooms, and a high-efficiency Bosch HVAC system. All major appliances—including kitchen appliances, oversized washer and dryer, and hot water heater—have been recently replaced. The main level features an open living room, galley-style kitchen, convenient half bath, and a versatile bonus room ideal for a dining area or home office. Sliding glass doors lead to a private rear deck with direct access to the parking area and spacious 21x10 garage. Upstairs, you’ll find two generously sized bedrooms and a full bath. Enjoy the benefits of a water-privileged community with access to a pool, pier, and boat docks. HOA fees cover fresh and wastewater, trash pickup, lawn care, shrub maintenance, roof and shingles, crawl space upkeep, exterior hose bib, pool, boat dock, fishing pier, and maintenance of common areas and entrance decking—providing low-maintenance living. Conveniently located for an easy commute to Rt. 50, Annapolis, and Easton, and within walking distance to restaurants and shopping.

1 Compass Cir Unit 2, Stevensville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

Selling Office: Maverick Realty, LLC.

$255,000

This charming 2 bedroom 1.5 bathroom condo located in a waterfront community which provides direct access to Thompson Creek which flows into Cox Creek offering fishing, crabbing and boating just steps away. This unit has new carpet upstairs,brand new stainless steel appliances in kitchen with tile floors. Beautiful hard wood floors in living area. Unit offers a one car garage.,additional off street parking and overflow area for guest parking.The community boasts a inground pool overlooking the creek, clubhouse and picnic area perfect for social gatherings. HOA fees also cover water,sewer and trash costs. Close to shopping, food, schools, parks, Kent Island Trail and Bay bridge. Home warranty provided. Slips are assigned by unit number and available for use only after purchase by unit owner. The current assigned slip located on Dock A is transferable for a one time fee of $3000.00

This charming 2 bedroom 1.5 bathroom condo located in a waterfront community which provides direct access to Thompson Creek which flows into Cox Creek offering fishing, crabbing and boating just steps away. This unit has new carpet upstairs,brand new stainless steel appliances in kitchen with tile floors. Beautiful hard wood floors in living area. Unit offers a one car garage.,additional off street parking and overflow area for guest parking.The community boasts a inground pool overlooking the creek, clubhouse and picnic area perfect for social gatherings. HOA fees also cover water,sewer and trash costs. Close to shopping, food, schools, parks, Kent Island Trail and Bay bridge. Home warranty provided. Slips are assigned by unit number and available for use only after purchase by unit owner. The current assigned slip located on Dock A is transferable for a one time fee of $3000.00

7 Mariners Way Unit #2, Stevensville

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

Selling Office: EXP Realty, LLC.

$255,000

This charming 2-bedroom, 1.5-bathroom townhouse offers a blend of modern comfort and community living. The interior features luxury vinyl plank and carpet and ceramic tile flooring in selected areas, complemented by a traditional floor plan. Enjoy cooking in the well-equipped kitchen with stainless steel appliances, including a dishwasher and microwave, and a convenient pantry. The main floor laundry adds to the ease of living. Step outside to discover community amenities, including an in-ground pool and access to Cox Creek for boating, fishing, and kayaking (community slips are on a wait list). The property includes an attached garage and additional off-street parking. Located in a vibrant neighborhood, residents benefit from nearby parks, excellent schools, and essential public services. The association maintains common areas, ensuring a well-kept environment. Experience a lifestyle that balances tranquility with community engagement in this delightful home.

This charming 2-bedroom, 1.5-bathroom townhouse offers a blend of modern comfort and community living. The interior features luxury vinyl plank and carpet and ceramic tile flooring in selected areas, complemented by a traditional floor plan. Enjoy cooking in the well-equipped kitchen with stainless steel appliances, including a dishwasher and microwave, and a convenient pantry. The main floor laundry adds to the ease of living. Step outside to discover community amenities, including an in-ground pool and access to Cox Creek for boating, fishing, and kayaking (community slips are on a wait list). The property includes an attached garage and additional off-street parking. Located in a vibrant neighborhood, residents benefit from nearby parks, excellent schools, and essential public services. The association maintains common areas, ensuring a well-kept environment. Experience a lifestyle that balances tranquility with community engagement in this delightful home.

5 Mariners Way Unit 2, Stevensville

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

Selling Office: The KW Collective.

$255,000

Beautifully updated 3BR/2BA end-unit in Kent Cove! Featuring beautiful hardwood floors bright & open living area with sliding door to private deck. Kitchen features stainless steel appliances, white cabinetry & quartz counters. New washer and dryer. Spacious primary suite plus 2 additional bedrooms, updated baths. 1-car garage. Community offers a pool, private pier, kayak launch & landscaped grounds. Minutes to Bay Bridge, shopping, dining & marinas. boat ramp nearby. Move-in ready – perfect for full-time living, weekend retreat, or investment!

Beautifully updated 3BR/2BA end-unit in Kent Cove! Featuring beautiful hardwood floors bright & open living area with sliding door to private deck. Kitchen features stainless steel appliances, white cabinetry & quartz counters. New washer and dryer. Spacious primary suite plus 2 additional bedrooms, updated baths. 1-car garage. Community offers a pool, private pier, kayak launch & landscaped grounds. Minutes to Bay Bridge, shopping, dining & marinas. boat ramp nearby. Move-in ready – perfect for full-time living, weekend retreat, or investment!

18 Mariners Way Unit 4, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Rosendale Realty.

$247,500

Welcome to country living ! Nestled on over an acre, this solid brick rancher offers nearly 2,000 square feet of living space with many possibilities. Enjoy the peace and privacy of a rural setting while still being conveniently located near Chestertown, Millington, and major commuter routes. The spacious lot provides room for gardening, recreation, hobbies, or simply enjoying the outdoors. Features include a garage, generous living areas, and the opportunity to customize and make this property your own. Whether you're looking for a primary residence, weekend retreat, or investment opportunity, this property offers potential in an Eastern Shore setting.

Welcome to country living ! Nestled on over an acre, this solid brick rancher offers nearly 2,000 square feet of living space with many possibilities. Enjoy the peace and privacy of a rural setting while still being conveniently located near Chestertown, Millington, and major commuter routes. The spacious lot provides room for gardening, recreation, hobbies, or simply enjoying the outdoors. Features include a garage, generous living areas, and the opportunity to customize and make this property your own. Whether you're looking for a primary residence, weekend retreat, or investment opportunity, this property offers potential in an Eastern Shore setting.

1904 Pondtown Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$240,200

BACK ON THE MARKET! Mold remediation was just completed! Seller is very motivated, Charming, well-kept rancher offering 3 bedrooms, 1 bath with a private 0.46 acre lot. Hardwood floors throughout gives the home character. Recently updated with fresh paint. Roof is 5 years old. New windows installed 2 years ago as well as a new shower. Paved driveway offers plenty of parking. New landscaping done as well as all electric being updated. Large shed in the yard. Located in the Kent Island Estates community and served by Matapeake schools. Minutes from bike trails, beaches as well as close to the Bay Bridge making it an easy commute. With no HOA headaches this property offers a lot of potential with space to grow. This home is being sold AS IS.

BACK ON THE MARKET! Mold remediation was just completed! Seller is very motivated, Charming, well-kept rancher offering 3 bedrooms, 1 bath with a private 0.46 acre lot. Hardwood floors throughout gives the home character. Recently updated with fresh paint. Roof is 5 years old. New windows installed 2 years ago as well as a new shower. Paved driveway offers plenty of parking. New landscaping done as well as all electric being updated. Large shed in the yard. Located in the Kent Island Estates community and served by Matapeake schools. Minutes from bike trails, beaches as well as close to the Bay Bridge making it an easy commute. With no HOA headaches this property offers a lot of potential with space to grow. This home is being sold AS IS.

300 Talbot Rd, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Witz Realty, LLC.

$239,000

Amazing 3-bedroom charming home in Grasonville, and It’s a just short walk to the famous Kent Narrows! Imagine curling up by a cozy brick and mason fireplace on those chilly nights. It’s like a blank canvas waiting for your creativity to shine. Looks small on the outside, but, it’s actually bigger on the inside! Wonderful screen porch just waiting for summer nights. Don’t miss out on this incredible opportunity for affordable living with endless possibilities.*Large storage building or shop out back!*Water access down the street that leads out to The Famous Kent Narrows! *Semi-private back yard that backs up to over 90 acres of county owned property.* Some water access at the end of Coursey Lane *No HOA or restrictions

Amazing 3-bedroom charming home in Grasonville, and It’s a just short walk to the famous Kent Narrows! Imagine curling up by a cozy brick and mason fireplace on those chilly nights. It’s like a blank canvas waiting for your creativity to shine. Looks small on the outside, but, it’s actually bigger on the inside! Wonderful screen porch just waiting for summer nights. Don’t miss out on this incredible opportunity for affordable living with endless possibilities.*Large storage building or shop out back!*Water access down the street that leads out to The Famous Kent Narrows! *Semi-private back yard that backs up to over 90 acres of county owned property.* Some water access at the end of Coursey Lane *No HOA or restrictions

117 Coursey Rd, Grasonville

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: RE/MAX Executive.

$236,000

INVESTOR ALERT! Looking to add a solid income-producing property to your portfolio? This charming duplex in the quaint town of Church Hill is the perfect opportunity. Each unit features a living room, kitchen, one bedroom, one bathroom, a washer/dryer, and separate metering. The property also offers a covered patio and convenient off-street parking. Both units are currently rented. Ideally located, this property is just a short drive to the picturesque historic towns of Chestertown and Centreville, with an easy commute to Easton, Annapolis, Middletown & Dover, DE, as well as the beautiful Maryland and Delaware beaches. Enjoy all that the Eastern Shore has to offer, including fishing, crabbing piers, playgrounds, bike and walking trails, parks, and so much more!

304 Main St, Church Hill

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

Selling Office: Benson & Mangold, LLC.

$230,000

Price improvement and ready to move in! Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a waterfront condominium community on Kent Island located minutes from Rt. 50 and a short walk to local dining and the Cross Island Trail. The community offers a club house, marina, pool, fitness center, pickleball, tennis, and racquetball courts, and social activities throughout the year. Schedule your tour today!

1 Beds ⋅ 1 Baths

Price improvement and ready to move in! Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a waterfront condominium community on Kent Island located minutes from Rt. 50 and a short walk to local dining and the Cross Island Trail. The community offers a club house, marina, pool, fitness center, pickleball, tennis, and racquetball courts, and social activities throughout the year. Schedule your tour today!

3 Queen Victoria Ct, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

$228,000

Selling Office: Non Subscribing Office.

221 Dutchess Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$222,500

Rarely available first floor condominium centrally located on Kent Island and in the Thompson Creek Community. Enjoy all the amenities of this water access community including the pool, tennis courts, clubhouse, and within a short walking distance to the water where you sit in a quiet community of proud homeowners. As you arrive, you will notice the peace and tranquility this community offers. Open the door and you will be greeted by the ample living room which features a cozy corner fireplace, plenty of sunlight that fills the home and sliders leading to the private covered balcony where you can enjoy views of the sunsets. Take advantage of the small outside storage closet. The kitchen provides everything a passionate cook needs to prepare even the most elaborate of meals. The primary bedroom features large windows, an ample closet and its private full bath. The other two bedrooms are equal in size and also offers sufficient space for a growing family. Another full bath can be found in the hallway. This condo offers PLENTY of parking and SUPER convenient location - less than 5 minutes to the Bay Bridge, Restaurants, Shopping, and ALL that the Island life has to offer.