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Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating extended family, or creating a private home office with serene water views. This deceivingly large 5-bedroom, 4-bath home features; extensive landscaping, lovely gazebo and brand-new roof.

5 Beds ⋅ 4 Baths

Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating extended family, or creating a private home office with serene water views. This deceivingly large 5-bedroom, 4-bath home features; extensive landscaping, lovely gazebo and brand-new roof.

302 Rosin Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$435,000

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3 bedrooms and 2.5 baths, along with a 2-car garage and a newly paved blacktop driveway. Inside, enjoy a bright, functional layout with brand-new carpet throughout the entire upstairs, giving the home a fresh, move-in-ready feel. Additional updates include a new roof, offering peace of mind for years to come. The spacious living areas flow seamlessly, making it ideal for both everyday living and entertaining. Step outside to a large backyard with plenty of space to relax and enjoy. The property includes a children’s play area and a vegetable garden, perfect for outdoor fun and homegrown produce. Highlights: 3 Bedrooms | 2.5 Bathrooms 1,784 Sq Ft | Built in 2004 2-Car Garage New Roof New Carpet Upstairs Blacktop Driveway Large Backyard Children’s Play Area Vegetable Garden Conveniently located just minutes from downtown Chestertown, Washington College, local shops, dining, and the waterfront, this home offers the perfect balance of peaceful living and accessibility. Schedule your showing today—this move-in-ready home won’t last long! Professional pictures coming 5/7 .

3 Beds ⋅ 3 Baths

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3 bedrooms and 2.5 baths, along with a 2-car garage and a newly paved blacktop driveway. Inside, enjoy a bright, functional layout with brand-new carpet throughout the entire upstairs, giving the home a fresh, move-in-ready feel. Additional updates include a new roof, offering peace of mind for years to come. The spacious living areas flow seamlessly, making it ideal for both everyday living and entertaining. Step outside to a large backyard with plenty of space to relax and enjoy. The property includes a children’s play area and a vegetable garden, perfect for outdoor fun and homegrown produce. Highlights: 3 Bedrooms | 2.5 Bathrooms 1,784 Sq Ft | Built in 2004 2-Car Garage New Roof New Carpet Upstairs Blacktop Driveway Large Backyard Children’s Play Area Vegetable Garden Conveniently located just minutes from downtown Chestertown, Washington College, local shops, dining, and the waterfront, this home offers the perfect balance of peaceful living and accessibility. Schedule your showing today—this move-in-ready home won’t last long! Professional pictures coming 5/7 .

215 Fairview Dr, Chestertown

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

Selling Office: Berkshire Hathaway Homeservice Homesale Realty.

$413,300

Charming 3-bedroom, 2-bathroom waterfront cottage nestled along the peaceful shores of Rosin Creek. Combining classic character with modern updates, the open floor plan creates a warm and inviting flow. Perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas. Updated flooring throughout the downstairs, which extends to the main floor master, complete with his and her closets. Refreshed bathrooms, skylights, and a brand-new rear porch extend the living space to the outdoors, where you can relax and take in the serene water views while being surrounded by nature. With direct access to the creek, this property offers the perfect blend of comfort, charm, and waterfront living.

3 Beds ⋅ 2 Baths

Charming 3-bedroom, 2-bathroom waterfront cottage nestled along the peaceful shores of Rosin Creek. Combining classic character with modern updates, the open floor plan creates a warm and inviting flow. Perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas. Updated flooring throughout the downstairs, which extends to the main floor master, complete with his and her closets. Refreshed bathrooms, skylights, and a brand-new rear porch extend the living space to the outdoors, where you can relax and take in the serene water views while being surrounded by nature. With direct access to the creek, this property offers the perfect blend of comfort, charm, and waterfront living.

600 Rosin Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$392,500

Your Dream Eastern Shore Retreat Awaits! Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting. Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from the family’s 1930s farm in Kennedyville. Just beyond, a spacious two-car garage provides convenience, while the backyard invites endless enjoyment with an above-ground pool, a deck, and a cozy fire pit. Inside, the galley kitchen boasts white cabinetry, granite countertops, and stainless steel appliances. Adjacent to the kitchen, a warm and inviting den features a wood stove, abundant natural light, and a spiral staircase leading to the private owner’s suite. The front of the home offers a welcoming sitting room, along with three comfortable bedrooms, a full hall bath, and a convenient laundry closet—all on the first floor. Upstairs, the expansive owner’s suite is a true sanctuary. Enter through a charming foyer into a space filled with natural light from grand portrait windows. Enjoy the oversized walk-in closet, vaulted ceilings, and a private balcony, plus a versatile nook ideal for a desk, workout space, or cozy reading corner. The ensuite bath is a spa-like retreat, featuring a jacuzzi tub, separate shower, dual sinks, and soaring ceilings. This Eastern Shore gem offers a lifestyle of comfort, character, and unforgettable moments. Don’t miss your chance to make it yours! Walk to the water, spend weekends in downtown Chestertown at the famous farmers market, shops or restaurants. Watch a game at Washington College, take a kayak out on the river or make a day trip to Easton, St. Michaels, Chesapeake City or Delaware. This property has everything you could want and No HOA. We have a quote for an alternate staircase install if the spiral staircase isn't your style. Seller is motivated and ready to pass this well maintained home to the next owners just in time for summer!

4 Beds ⋅ 2 Baths

Your Dream Eastern Shore Retreat Awaits! Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting. Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from the family’s 1930s farm in Kennedyville. Just beyond, a spacious two-car garage provides convenience, while the backyard invites endless enjoyment with an above-ground pool, a deck, and a cozy fire pit. Inside, the galley kitchen boasts white cabinetry, granite countertops, and stainless steel appliances. Adjacent to the kitchen, a warm and inviting den features a wood stove, abundant natural light, and a spiral staircase leading to the private owner’s suite. The front of the home offers a welcoming sitting room, along with three comfortable bedrooms, a full hall bath, and a convenient laundry closet—all on the first floor. Upstairs, the expansive owner’s suite is a true sanctuary. Enter through a charming foyer into a space filled with natural light from grand portrait windows. Enjoy the oversized walk-in closet, vaulted ceilings, and a private balcony, plus a versatile nook ideal for a desk, workout space, or cozy reading corner. The ensuite bath is a spa-like retreat, featuring a jacuzzi tub, separate shower, dual sinks, and soaring ceilings. This Eastern Shore gem offers a lifestyle of comfort, character, and unforgettable moments. Don’t miss your chance to make it yours! Walk to the water, spend weekends in downtown Chestertown at the famous farmers market, shops or restaurants. Watch a game at Washington College, take a kayak out on the river or make a day trip to Easton, St. Michaels, Chesapeake City or Delaware. This property has everything you could want and No HOA. We have a quote for an alternate staircase install if the spiral staircase isn't your style. Seller is motivated and ready to pass this well maintained home to the next owners just in time for summer!

128 Edmore Rd, Chestertown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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

$379,000

Fully remodeled by reputable licensed contractor and subcontractors, 104 Iris has had a glow-up and is ready for showing! The clean lines of the new quartz countertops, the weight of soft golden Amerock hardware, Moen fixtures, Wolf two-tone shaker style cabinetry and well-appointed subway tile set the stage in the beautiful new Kitchen and bathrooms. Where a modern feel is met with the softness and simplicity of Neutrals as you move throughout the rooms that offer a timeless yet 2026 vibe! High-quality, low-maintenance LVP flooring has been installed in all high-traffic areas, along with carpet to quiet the bedroom spaces. Many new energy-saving features include architectural shingles, R38 insulation in the attic, crawl encapsulation, new HVAC unit & dehumidifier. Entry from the rear deck and hall to the large laundry area, is conveniently located adjacent to the hub of the home; the kitchen, where it balances aesthetics with functionality. Ample storage, Stainless steel appliances, an "L" shaped counter with seating area, giving all the practical space for your family's needs on one level. Electric has been modernized with new fixtures, premium touch mirrors, multiple remote-operated ceiling fans, USB outlets & recessed lighting. New doors, hardware and keypad entry locks, round out another set of upgrades. Solar lighting, fresh landscaping, and new treated decking enhance the exterior. It's large lot with mature trees, sits back off the road, in a quiet cul-de-sac, offering privacy, safety, and comfort. Backing up to acres of farmland, an extended outdoor living space great for entertaining also provides opportunity for viewing wildlife and sunsets alike. 104 Iris brings rural community living with the convenience of being close to town. Located in the Chester Harbor community in Queen Anne's county, where a 5-minute drive will have you centered in the town of Chestertown, known for its historic charm, river access, and boating opportunities, offering convenient commutes and amenities. Within walking distance of a private community water access and playground, this home has every detail ironed out and waiting for you! Easy to show! Join the Community Association, which is very reasonable and provides water access.

3 Beds ⋅ 2 Baths

Fully remodeled by reputable licensed contractor and subcontractors, 104 Iris has had a glow-up and is ready for showing! The clean lines of the new quartz countertops, the weight of soft golden Amerock hardware, Moen fixtures, Wolf two-tone shaker style cabinetry and well-appointed subway tile set the stage in the beautiful new Kitchen and bathrooms. Where a modern feel is met with the softness and simplicity of Neutrals as you move throughout the rooms that offer a timeless yet 2026 vibe! High-quality, low-maintenance LVP flooring has been installed in all high-traffic areas, along with carpet to quiet the bedroom spaces. Many new energy-saving features include architectural shingles, R38 insulation in the attic, crawl encapsulation, new HVAC unit & dehumidifier. Entry from the rear deck and hall to the large laundry area, is conveniently located adjacent to the hub of the home; the kitchen, where it balances aesthetics with functionality. Ample storage, Stainless steel appliances, an "L" shaped counter with seating area, giving all the practical space for your family's needs on one level. Electric has been modernized with new fixtures, premium touch mirrors, multiple remote-operated ceiling fans, USB outlets & recessed lighting. New doors, hardware and keypad entry locks, round out another set of upgrades. Solar lighting, fresh landscaping, and new treated decking enhance the exterior. It's large lot with mature trees, sits back off the road, in a quiet cul-de-sac, offering privacy, safety, and comfort. Backing up to acres of farmland, an extended outdoor living space great for entertaining also provides opportunity for viewing wildlife and sunsets alike. 104 Iris brings rural community living with the convenience of being close to town. Located in the Chester Harbor community in Queen Anne's county, where a 5-minute drive will have you centered in the town of Chestertown, known for its historic charm, river access, and boating opportunities, offering convenient commutes and amenities. Within walking distance of a private community water access and playground, this home has every detail ironed out and waiting for you! Easy to show! Join the Community Association, which is very reasonable and provides water access.

104 Iris Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: RE/MAX Executive.

$349,000

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

3 Beds ⋅ 2 Baths

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$330,000

Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

3 Beds ⋅ 2 Baths

Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13

129 Parma Rd, Chestertown

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

Selling Office: Benson & Mangold, LLC.

$322,000

Delightful Ranch Home In Chester Harbor. Step into this inviting ranch-style home featuring a smart split-bedroom layout and two full baths, offering comfort and privacy for all. Fresh new flooring throughout adds a clean, modern feel . The spacious updated eat-in kitchen is perfect for casual meals or entertaining guests. Unwind in the charming living room, where a cozy fireplace sets the scene for relaxing evenings. A separate laundry room with its own exterior entrance adds everyday convenience. Recent upgrades—including a new roof (2017) and a reverse osmosis water filtration system—provide peace of mind and added value. Outside, enjoy the rear deck, ideal for morning coffee, weekend barbecues, or simply quiet time. Chester Harbor is a waterfront community with optional waterfront privileges for just $15/year and no HOA. Located in Queen Anne’s County, you’re close to historic Chestertown and Washington College for dining, shopping, and year-round events. AHS Home Warranty Included.

3 Beds ⋅ 2 Baths

Delightful Ranch Home In Chester Harbor. Step into this inviting ranch-style home featuring a smart split-bedroom layout and two full baths, offering comfort and privacy for all. Fresh new flooring throughout adds a clean, modern feel . The spacious updated eat-in kitchen is perfect for casual meals or entertaining guests. Unwind in the charming living room, where a cozy fireplace sets the scene for relaxing evenings. A separate laundry room with its own exterior entrance adds everyday convenience. Recent upgrades—including a new roof (2017) and a reverse osmosis water filtration system—provide peace of mind and added value. Outside, enjoy the rear deck, ideal for morning coffee, weekend barbecues, or simply quiet time. Chester Harbor is a waterfront community with optional waterfront privileges for just $15/year and no HOA. Located in Queen Anne’s County, you’re close to historic Chestertown and Washington College for dining, shopping, and year-round events. AHS Home Warranty Included.

105 Parma Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$317,000

Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This property has a lot to offer!

3 Beds ⋅ 2 Baths

Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This property has a lot to offer!

213 Central Dr, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$300,000

Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy efficient commuting and quick access to Chestertown, Church Hill, Centreville, Easton, and Kent Island. Inside the home, enjoy an updated full bath, a new HVAC system and well pump, a six year old septic system (flushed in 2025), as well as a large, partially finished basement - perfect for storage.

3 Beds ⋅ 1 Baths

Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy efficient commuting and quick access to Chestertown, Church Hill, Centreville, Easton, and Kent Island. Inside the home, enjoy an updated full bath, a new HVAC system and well pump, a six year old septic system (flushed in 2025), as well as a large, partially finished basement - perfect for storage.

154 Longfellow Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: CR Realty.

$295,000

Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little TLC and updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and plenty of ways to experience the scenic beauty of the Chester River. The area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore. NOTE: Virtually staged/digitally enhanced photos. Images are for illustrative purposes and may not represent the property's current condition or actual furnishings.

3 Beds ⋅ 2 Baths

Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little TLC and updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and plenty of ways to experience the scenic beauty of the Chester River. The area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore. NOTE: Virtually staged/digitally enhanced photos. Images are for illustrative purposes and may not represent the property's current condition or actual furnishings.

240 Round Top Rd, Chestertown

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

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

$289,000

An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been freshly painted with LPV flooring and carpet throughout. This home offers the ultimate in conveniences local public and private golf courses outlets Close Proximity to the Chester River, fine dining and easy access to major highways. Don't miss out on the chance to create your dream space in this prime Chestertown location! NEW HVAC SYSTEM TO BE INSTALLED

3 Beds ⋅ 1 Baths

An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been freshly painted with LPV flooring and carpet throughout. This home offers the ultimate in conveniences local public and private golf courses outlets Close Proximity to the Chester River, fine dining and easy access to major highways. Don't miss out on the chance to create your dream space in this prime Chestertown location! NEW HVAC SYSTEM TO BE INSTALLED

517 Round Top Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$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.

3 Beds ⋅ 1 Baths

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.

$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!

3 Beds ⋅ 2 Baths

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.

$228,000

3 Beds ⋅ 2 Baths

221 Dutchess Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Non Subscribing Office.