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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.

$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.

$325,000

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

3 Beds ⋅ 2 Baths

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

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

Selling Office: Coldwell Banker Realty.

$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.

$228,000

3 Beds ⋅ 2 Baths

221 Dutchess Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Non Subscribing Office.

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