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Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler is perfectly situated on an oversized double lot, offering both comfort and exceptional outdoor space. From the moment you arrive, you’ll appreciate the care and attention this home has received, making it truly move-in ready. Step inside to a bright and inviting open floor plan designed for easy living and entertaining. The spacious living room features a soaring cathedral ceiling and a ceiling fan, creating an airy and welcoming atmosphere. This space flows seamlessly into the kitchen and dining area, allowing for effortless gatherings with family and friends. The dining area is enhanced by a beautiful custom chair rail molding detail that adds character and elegance, while sliding glass doors provide abundant natural light and direct access to the backyard, perfect for indoor-outdoor living. The kitchen is both functional and stylish, offering warm wood cabinetry, recessed lighting, and a vaulted ceiling that adds to the home’s open and spacious feel. The bedroom area includes a comfortable primary suite complete with a private ensuite bath, along with two additional bedrooms, each featuring ceiling fans for year-round comfort. A well-appointed hall bath conveniently serves the two additional bedrooms, providing both functionality and privacy for family members or guests. Step outside and discover an incredible backyard retreat that truly sets this property apart. Fully enclosed with a privacy fence, the expansive yard offers plenty of room to relax, play, or entertain. Enjoy evenings on the patio, stroll along the walking paths, or unwind under the beautiful gazebo. A cozy fire pit creates the perfect gathering spot for cooler nights. One of the standout features of this property is the impressive three-bay workshop with electric, ideal for hobbyists, craftsmen, or anyone in need of substantial workspace and storage. With its thoughtful updates, inviting layout, and exceptional outdoor amenities, this home offers a rare opportunity to enjoy both comfort and versatility in a peaceful setting.

3 Beds ⋅ 2 Baths

Meticulously maintained and full of charm, this delightful three-bedroom, two-bath rambler is perfectly situated on an oversized double lot, offering both comfort and exceptional outdoor space. From the moment you arrive, you’ll appreciate the care and attention this home has received, making it truly move-in ready. Step inside to a bright and inviting open floor plan designed for easy living and entertaining. The spacious living room features a soaring cathedral ceiling and a ceiling fan, creating an airy and welcoming atmosphere. This space flows seamlessly into the kitchen and dining area, allowing for effortless gatherings with family and friends. The dining area is enhanced by a beautiful custom chair rail molding detail that adds character and elegance, while sliding glass doors provide abundant natural light and direct access to the backyard, perfect for indoor-outdoor living. The kitchen is both functional and stylish, offering warm wood cabinetry, recessed lighting, and a vaulted ceiling that adds to the home’s open and spacious feel. The bedroom area includes a comfortable primary suite complete with a private ensuite bath, along with two additional bedrooms, each featuring ceiling fans for year-round comfort. A well-appointed hall bath conveniently serves the two additional bedrooms, providing both functionality and privacy for family members or guests. Step outside and discover an incredible backyard retreat that truly sets this property apart. Fully enclosed with a privacy fence, the expansive yard offers plenty of room to relax, play, or entertain. Enjoy evenings on the patio, stroll along the walking paths, or unwind under the beautiful gazebo. A cozy fire pit creates the perfect gathering spot for cooler nights. One of the standout features of this property is the impressive three-bay workshop with electric, ideal for hobbyists, craftsmen, or anyone in need of substantial workspace and storage. With its thoughtful updates, inviting layout, and exceptional outdoor amenities, this home offers a rare opportunity to enjoy both comfort and versatility in a peaceful setting.

2032 Pondtown Rd, Chestertown

Listing courtesy of Northrop Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$332,000

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 3 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 quartz counters, SS appliances, and a neutral 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. 2 additional bedrooms add options for an office or study. The expansive deck offers views of a private, level lot backing to woods. Chestertown is a quaint, historic district on the Eastern Shore with an avid 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 $12,000 that can be paid off with installments, annually over 15-20 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE. THERE ARE SEVERAL OTHER HOMES CURRENTLY AVAILABLE AND COMING

3 Beds ⋅ 2 Baths

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 3 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 quartz counters, SS appliances, and a neutral 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. 2 additional bedrooms add options for an office or study. The expansive deck offers views of a private, level lot backing to woods. Chestertown is a quaint, historic district on the Eastern Shore with an avid 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 $12,000 that can be paid off with installments, annually over 15-20 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE. THERE ARE SEVERAL OTHER HOMES CURRENTLY AVAILABLE AND COMING

11035 Bottom Rd, Worton

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

Selling Office: Coldwell Banker Realty.

$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.

$220,000

Ready for your next investment with built-in equity? 513 Round Top Rd presents a fantastic opportunity for homeowners and investors who love forced appreciation! With all major systems in place, this 4bd/1ba rancher ready for your vision without breaking the bank. Simple cosmetic improvements can make this home rent ready or produce a nice profit on a fix and flip. Being sold as is. Bring your contractor and vision today!

4 Beds ⋅ 1 Baths

Ready for your next investment with built-in equity? 513 Round Top Rd presents a fantastic opportunity for homeowners and investors who love forced appreciation! With all major systems in place, this 4bd/1ba rancher ready for your vision without breaking the bank. Simple cosmetic improvements can make this home rent ready or produce a nice profit on a fix and flip. Being sold as is. Bring your contractor and vision today!

513 Round Top Rd, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Century 21 Don Gurney.

$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.

3 Beds ⋅ 1 Baths

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.

100 Prospect St, Chestertown

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

Selling Office: Bayside Realty.

$195,000

Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

3 Beds ⋅ 1 Baths

Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

139 Prospect St, Chestertown

Listing courtesy of Redfin Corp. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$155,000

Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the home’s Clean, Contemporary Feel. Major Updates Include a Brand New HVAC System (2026) and New Windows (2026) for Energy Efficiency, Much More! Relax on the Inviting Covered Front Porch and Enjoy a Truly Move-In Ready Home Designed to Impress.

2 Beds ⋅ 1 Baths

Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the home’s Clean, Contemporary Feel. Major Updates Include a Brand New HVAC System (2026) and New Windows (2026) for Energy Efficiency, Much More! Relax on the Inviting Covered Front Porch and Enjoy a Truly Move-In Ready Home Designed to Impress.

132 Prospect St, Chestertown

Listing courtesy of ANR Realty, LLC. Contact:

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