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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.

$264,900

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.

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.

101 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$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.

$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:

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.

$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.

107 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$255,000

Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

318 Lincoln, Chestertown

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

Selling Office: Samson Properties of DE, LLC.

$250,000

This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed—perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.

This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed—perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.

112 Metcalf Rd, Chestertown

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$250,000

Welcome to 124 Char Nor Manor Blvd, a charming home tucked away on a quiet street in Chestertown. This residence offers the perfect balance of comfort, convenience, and lifestyle, all within the highly sought-after Queen Anne’s County school district. Step inside to find a warm and inviting space with high ceilings and skylights flooded with tons of natural lighting. Continue into the living room where a cozy wood stove becomes the heart of the home during cooler months. A few upgrades worth mentioning- Freshly Painted Interior & Shutters, Restored Back Deck & Front Stairwell. Outside, the fully fenced backyard provides plenty of space for pets, play, or gardening, while offering peace of mind and privacy. You’ll love spending evenings on the back deck, enjoying the quiet neighborhood setting. Located in a desirable water-oriented community, residents enjoy the natural beauty of the Chester River just across the street! If you’ve been searching for a home that combines small-town charm, a strong school district, and water-inspired living, look no further, 124 Char Nor Manor Blvd is ready to welcome you home!

2 Beds ⋅ 2 Baths

Welcome to 124 Char Nor Manor Blvd, a charming home tucked away on a quiet street in Chestertown. This residence offers the perfect balance of comfort, convenience, and lifestyle, all within the highly sought-after Queen Anne’s County school district. Step inside to find a warm and inviting space with high ceilings and skylights flooded with tons of natural lighting. Continue into the living room where a cozy wood stove becomes the heart of the home during cooler months. A few upgrades worth mentioning- Freshly Painted Interior & Shutters, Restored Back Deck & Front Stairwell. Outside, the fully fenced backyard provides plenty of space for pets, play, or gardening, while offering peace of mind and privacy. You’ll love spending evenings on the back deck, enjoying the quiet neighborhood setting. Located in a desirable water-oriented community, residents enjoy the natural beauty of the Chester River just across the street! If you’ve been searching for a home that combines small-town charm, a strong school district, and water-inspired living, look no further, 124 Char Nor Manor Blvd is ready to welcome you home!

124 Char Nor Manor Blvd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Compass.

$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.

$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.

$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

🏡 💎 Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K 🎉 Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! ✨ Your Dream Home Checklist: ✅ * NO HOA! Freedom & Savings! 💸 * One-Level Living: Easy breezy! 🚶‍♀️ * Open Concept: Perfect for entertaining! 🛋️ The heart of the home is the spectacular eat-in kitchen! You'll love the white shaker cabinets, dazzling granite countertops, and sleek stainless steel appliances. 🍳 The main areas feature gorgeous LVP flooring, while cozy carpet warms the bedrooms. Step outside to your private covered patio for morning coffee ☕ or evening relaxation. 🌞 With a generous 5,914 sq ft lot, there's plenty of room for fun! 🌳 Retreat to your private primary suite 👑 with a spa-like en-suite and walk-in shower. 🚿 Embrace the Chestertown Life! ⚓ This prime spot is minutes from historic downtown charm! Enjoy the weekly farmers market 🥕, shops, galleries 🖼️, and waterfront festivals like the famous Downrigging Weekend ⛵. This golden opportunity won't last long! Be the first to call this exquisite property "home." 🔑 Your new beginning starts here! ❤️

🏡 💎 Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K 🎉 Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! ✨ Your Dream Home Checklist: ✅ * NO HOA! Freedom & Savings! 💸 * One-Level Living: Easy breezy! 🚶‍♀️ * Open Concept: Perfect for entertaining! 🛋️ The heart of the home is the spectacular eat-in kitchen! You'll love the white shaker cabinets, dazzling granite countertops, and sleek stainless steel appliances. 🍳 The main areas feature gorgeous LVP flooring, while cozy carpet warms the bedrooms. Step outside to your private covered patio for morning coffee ☕ or evening relaxation. 🌞 With a generous 5,914 sq ft lot, there's plenty of room for fun! 🌳 Retreat to your private primary suite 👑 with a spa-like en-suite and walk-in shower. 🚿 Embrace the Chestertown Life! ⚓ This prime spot is minutes from historic downtown charm! Enjoy the weekly farmers market 🥕, shops, galleries 🖼️, and waterfront festivals like the famous Downrigging Weekend ⛵. This golden opportunity won't last long! Be the first to call this exquisite property "home." 🔑 Your new beginning starts here! ❤️

100 Metcalf Rd, Chestertown

Listing courtesy of Bayside Realty. Contact:

Selling Office: Douglas Realty LLC.

$235,000

Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and central heat/air. Competitively priced and full of potential!

Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and central heat/air. Competitively priced and full of potential!

7521 Pine Ave, Chestertown

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

Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside the primary bedroom. This property is at the end of Metcalf Rd.

$230,000

Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside the primary bedroom. This property is at the end of Metcalf Rd.

126 Metcalf Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Benson & Mangold, LLC..

$228,000

Selling Office: Non Subscribing Office.

221 Dutchess Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$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.

$220,000

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.

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.

$205,000

Take advantage of the Eastern Shore's amenities and quality of life in this low maintenance one floor home just a hop and a skip from the Chesapeake Bay and public beach. The Sergeant's Quarters at Tolchester Village is located less than 15 minutes from both Chestertown and Rock Hall providing nearby cultural, entertainment, and employment opportunities. The home itself has been taken care of with love and is ready for its next steward. Vaulted ceilings and spacious room sizes provide a great feel. The Shanty Bar at Tolchester Marina, just a beach cruiser or golf cart ride away, is one of the Chesapeake Bay's premier beachfront establishments serving coastal fare, fresh made boat drinks, and hosting live music on the Bay. Invest wisely in this tranquil retreat with bountiful nearby attractions.

Take advantage of the Eastern Shore's amenities and quality of life in this low maintenance one floor home just a hop and a skip from the Chesapeake Bay and public beach. The Sergeant's Quarters at Tolchester Village is located less than 15 minutes from both Chestertown and Rock Hall providing nearby cultural, entertainment, and employment opportunities. The home itself has been taken care of with love and is ready for its next steward. Vaulted ceilings and spacious room sizes provide a great feel. The Shanty Bar at Tolchester Marina, just a beach cruiser or golf cart ride away, is one of the Chesapeake Bay's premier beachfront establishments serving coastal fare, fresh made boat drinks, and hosting live music on the Bay. Invest wisely in this tranquil retreat with bountiful nearby attractions.

21363 Lynn Ln, Chestertown

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

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.

$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.

139 Prospect St, Chestertown

Listing courtesy of Redfin Corp. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$190,000

Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely updated with all new fixtures and finishes. The main level offers ample living space, dinging room and new kitchen and laundry. Upstairs you will find three bedrooms and a full bathroom, with access from the primary bedroom as well. Outside, enjoy a newly fenced backyard, updated shed, and an extra-deep lot offering the potential for additional rear parking. A new roof installed in 2024 adds even more value and peace of mind. Boasting generous space and extensive upgrades throughout, this home presents an exceptional opportunity for a primary residence, weekend getaway, or investment property. Ideally located just moments from downtown shopping, dining, and the waterfront, you’ll love the walkable lifestyle and charm that Chestertown has to offer.

Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely updated with all new fixtures and finishes. The main level offers ample living space, dinging room and new kitchen and laundry. Upstairs you will find three bedrooms and a full bathroom, with access from the primary bedroom as well. Outside, enjoy a newly fenced backyard, updated shed, and an extra-deep lot offering the potential for additional rear parking. A new roof installed in 2024 adds even more value and peace of mind. Boasting generous space and extensive upgrades throughout, this home presents an exceptional opportunity for a primary residence, weekend getaway, or investment property. Ideally located just moments from downtown shopping, dining, and the waterfront, you’ll love the walkable lifestyle and charm that Chestertown has to offer.

423 Calvert St, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$190,000

Discover a rare opportunity to create your future home on this beautiful parcel of land, set in a peaceful and scenic setting. With ample space and flexibility, the property offers endless possibilities for a custom build, from a cozy retreat to a thoughtfully designed estate. Enjoy the tranquility of country living while remaining conveniently close to local shops, dining, and nearby routes for easy access. This is more than just land — it’s an opportunity to shape a lifestyle connected to nature and comfort. McCrone engineer engaged; initial field work has begun, including coordination with county departments. Two (2) acres have been removed from the Woodland Program and AG transfer tax has been paid which is instant savings. Perc Approved and was recently re-evaluated by the QA Environmental Health Department. Confirm with QA Environmental Health.

Hoffecker Road, Chestertown

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

Selling Office: EXIT Preferred Realty.

$185,000

Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.

Lot 9 Prestwick, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

9925 Flatland Rd, Chestertown

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Non Subscribing Office.

$175,000

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem!

2 Beds ⋅ 1 Baths

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem!

21324 Persimmon Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Douglas Realty LLC.

$175,000

OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here -- just bring your ideas and your tools and make it shine again. Close to Chestertown while enjoying the benefits of Queen Anne's County living!

OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here -- just bring your ideas and your tools and make it shine again. Close to Chestertown while enjoying the benefits of Queen Anne's County living!

113 Pear Tree Point Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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

$175,000

Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Renters finally moved out and the house is being cleaned up. Roof was replaced in 2022.

2 Beds

Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Renters finally moved out and the house is being cleaned up. Roof was replaced in 2022.

23069 Raleigh Rd, Chestertown

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