$3,995,000 Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house. 3 Beds ⋅ 4 Baths Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house. 240 Round Top Landing Rd, Chestertown Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344
$3,000,000 87-acre tract located Northwest of Chestertown. Land tract was annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The land is approximately 44 acres of tillable and 48 acres of timber. The farmland is surrounded by a forested buffer and may nicely serve the future layout and privacy of a residential community. Site plans and previous preliminary designs are available to review to guide future planning on the property and can be provided. 87-acre tract located Northwest of Chestertown. Land tract was annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The land is approximately 44 acres of tillable and 48 acres of timber. The farmland is surrounded by a forested buffer and may nicely serve the future layout and privacy of a residential community. Site plans and previous preliminary designs are available to review to guide future planning on the property and can be provided. Flatland Road, Chestertown Listing courtesy of The Land Group. Contact: (410) 934-3478
$1,765,000 Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or Rock Hall. Enjoy the wildlife, rural setting, and inground pool. Native plants create a very nicely landscaped home. All wall paneling is Western Red Cedar and the wood floors are 150+ years old heart pine. The game room could be used as bedroom #5. The family room has a brick wood burning fireplace, table space , breakfast bar, and exposed wood beams. Sign posted. Owner Agent. 5 Beds ⋅ 5 Baths Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or Rock Hall. Enjoy the wildlife, rural setting, and inground pool. Native plants create a very nicely landscaped home. All wall paneling is Western Red Cedar and the wood floors are 150+ years old heart pine. The game room could be used as bedroom #5. The family room has a brick wood burning fireplace, table space , breakfast bar, and exposed wood beams. Sign posted. Owner Agent. 22900 Handy Point Road Handy Point Rd, Chestertown Listing courtesy of Davis Real Estate, Inc.. Contact: 410-778-2610
$1,725,000 SMITH-RINGGOLD HOUSE. ca. 1750 This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified representing four defined periods and enlarged over the course of its 250-year history. William Ringgold added rooms toward the River in about 1759 that doubled the space. (Often, one would find 18th c. additions such as this creating a telescope style design. ) The present owner took two-years to restore the home from foundation to attic. A river-side sun-porch/breakfact room was added. ,The cedar shingle roof, , plumbing, wiring, heat and A/C systems were added or replaced. Wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street sounds. Aside from your own personal touches, this house awaits our arrival anf iss prepared for the next century. The ground floor has a large double parlor, serene sitting room, formal dining room, breakfast room, and a stunning Chef’s kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a “secret” staff stairway. The third floor has a large sitting room, bathroom, and fourth bedroom. A setion of the home’s original c. 1750 roof has been restored forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River eliminating the fear of flooding. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artist’s studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Chestertown in the County of Kent is "a place where one would rather be". Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today, Chestertown, is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders. 4 Beds ⋅ 5 Baths SMITH-RINGGOLD HOUSE. ca. 1750 This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified representing four defined periods and enlarged over the course of its 250-year history. William Ringgold added rooms toward the River in about 1759 that doubled the space. (Often, one would find 18th c. additions such as this creating a telescope style design. ) The present owner took two-years to restore the home from foundation to attic. A river-side sun-porch/breakfact room was added. ,The cedar shingle roof, , plumbing, wiring, heat and A/C systems were added or replaced. Wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street sounds. Aside from your own personal touches, this house awaits our arrival anf iss prepared for the next century. The ground floor has a large double parlor, serene sitting room, formal dining room, breakfast room, and a stunning Chef’s kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a “secret” staff stairway. The third floor has a large sitting room, bathroom, and fourth bedroom. A setion of the home’s original c. 1750 roof has been restored forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River eliminating the fear of flooding. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artist’s studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Chestertown in the County of Kent is "a place where one would rather be". Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today, Chestertown, is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders. 201 N Water St, Chestertown Listing courtesy of Maryland Heritage Properties. Contact: (443) 480-7342
$1,525,000 Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood. 5 Beds ⋅ 5 Baths Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood. 22956 Fairgale Farm Ln, Chestertown Listing courtesy of Doug Ashley Realtors, LLC. Contact:
$1,499,000 Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! 3 Beds ⋅ 4 Baths Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! Little Harbor Way Unit #1, Chestertown Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$995,000 Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away. 3 Beds ⋅ 4 Baths Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away. 230 S Water St Unit #1, Chestertown Listing courtesy of Gunther-McClary Real Estate. Contact:
$995,000 Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. 3 Beds ⋅ 4 Baths Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. 226 S Water St, Chestertown Listing courtesy of Gunther-McClary Real Estate. Contact:
$950,000 Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away. 3 Beds ⋅ 4 Baths Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away. 228 S Water St, Chestertown Listing courtesy of Gunther-McClary Real Estate. Contact:
$949,900 Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! 4 Beds ⋅ 4 Baths Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! Landing Ln Unit #25, Chestertown Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$900,000 List price to be opening bid at online only auction. Auction to take place to the Auctioneer's website. Bidding begins Saturday, April 6th & ends Thursday, April 11, 2024 at 12:00 pm. Exceptional opportunity to purchase a 12-Unit Apartment Complex comprised of 3 adjacent buildings. 11 out of 12 units are currently rented. Location: Chestertown is in Kent County; the apartment complex is conveniently located just a few blocks over the Chester River Bridge (Rte 213). The property has a convenient location near dining, shopping, schools, recreational facilities, and access to transportation routes. The building is located blocks away from Washington College, the University of MD Medical Center and the Downtown Historic District. **Current Gross Monthly Scheduled Rent of $14,044** **Current Annual Gross Scheduled Rent of $168,528** Each Unit is a 1 bedroom, 1 bath single level apartment. Rent Roll: 321 Calvert St rented for $1050/month. 323 Calvert St rented for $920/month. 325 Calvert St rented for $1150/month. 327 Calvert St rented for $1300/month. 329 Calvert St rented for $900/month. 331 Calvert St currently vacant. 333 Calvert St rented for $1180/month. 335 Calvert St rented for $1299/month. 337 Calvert St rented for $1445/month. 339 Calvert St rented for $1400/month. 341 Calvert St rented for $1200/month. 343 Calvert St rented for $1200/month. Annual expenses are approximate: $4,200 for insurance, $4,000 for water/sewer, $1,200 for lawn care, $2,500 for maintenance $1,600 for Gas/electric. List price to be opening bid at online only auction. Auction to take place to the Auctioneer's website. Bidding begins Saturday, April 6th & ends Thursday, April 11, 2024 at 12:00 pm. Exceptional opportunity to purchase a 12-Unit Apartment Complex comprised of 3 adjacent buildings. 11 out of 12 units are currently rented. Location: Chestertown is in Kent County; the apartment complex is conveniently located just a few blocks over the Chester River Bridge (Rte 213). The property has a convenient location near dining, shopping, schools, recreational facilities, and access to transportation routes. The building is located blocks away from Washington College, the University of MD Medical Center and the Downtown Historic District. **Current Gross Monthly Scheduled Rent of $14,044** **Current Annual Gross Scheduled Rent of $168,528** Each Unit is a 1 bedroom, 1 bath single level apartment. Rent Roll: 321 Calvert St rented for $1050/month. 323 Calvert St rented for $920/month. 325 Calvert St rented for $1150/month. 327 Calvert St rented for $1300/month. 329 Calvert St rented for $900/month. 331 Calvert St currently vacant. 333 Calvert St rented for $1180/month. 335 Calvert St rented for $1299/month. 337 Calvert St rented for $1445/month. 339 Calvert St rented for $1400/month. 341 Calvert St rented for $1200/month. 343 Calvert St rented for $1200/month. Annual expenses are approximate: $4,200 for insurance, $4,000 for water/sewer, $1,200 for lawn care, $2,500 for maintenance $1,600 for Gas/electric. 343 Calvert St, Chestertown Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:
$895,000 Commercial Development Site on busy MD Rte 213, Prime location across from Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available. Commercial Development Site on busy MD Rte 213, Prime location across from Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available. 515 Washington Ave, Chestertown Listing courtesy of EShore. Contact:
$805,000 Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! 3 Beds ⋅ 4 Baths Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! Landing Ln Unit #11, Chestertown Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$725,000 Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! 3 Beds ⋅ 3 Baths Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more! Landing Ln Unit #37, Chestertown Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$695,000 This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel driveway on North Water Street. A pair of new wood gates define the entry to the oasis. The redesigned flow of the first floor provides well for the intended purpose of both entertaining and home comfort. A den, powder room, and elevator adjoin the two-story, sun-filled foyer. A large living room with gas fireplace and separate dining room (with doors to the rear brick patio and raised beds) provide the pathway to a beautifully designed large island kitchen with breakfast area with bay window. Mudroom with sink, full sized washer and dryer and storage is adjacent to a side entry and double garage with EV charging station. Floor two comprises mostly a primary suite that includes bath, large office and exercise space with access to a very large, insulated and conditioned storage space (easily repurposed to a games room or home theatre), a guest bedroom and hall bath. The third-floor features two additional bedrooms and bath with large amounts of closet space. Recently installed solar panels, discreetly positioned, have resulted in nearly net zero energy expense. 4 Beds ⋅ 4 Baths This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel driveway on North Water Street. A pair of new wood gates define the entry to the oasis. The redesigned flow of the first floor provides well for the intended purpose of both entertaining and home comfort. A den, powder room, and elevator adjoin the two-story, sun-filled foyer. A large living room with gas fireplace and separate dining room (with doors to the rear brick patio and raised beds) provide the pathway to a beautifully designed large island kitchen with breakfast area with bay window. Mudroom with sink, full sized washer and dryer and storage is adjacent to a side entry and double garage with EV charging station. Floor two comprises mostly a primary suite that includes bath, large office and exercise space with access to a very large, insulated and conditioned storage space (easily repurposed to a games room or home theatre), a guest bedroom and hall bath. The third-floor features two additional bedrooms and bath with large amounts of closet space. Recently installed solar panels, discreetly positioned, have resulted in nearly net zero energy expense. 106 Water St N Unit #1/2, Chestertown Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$649,900 (Pics are from a prior listing. New pics on the way) Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you name it. 15 acres, with small pond and open areas for your animals, sports field, fire pit or huge gardens. Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or biking trail and hunting possible all part of what makes this place a dream come true. In the home enjoy large family room with propane fireplace, beautiful kitchen with stainless steel appliances and granite counters. Custom cabinets and built-ins, wood, laminate, and tile floors throughout. Entry level and second level bedrooms. Ready to relax head to the screened porch for quiet evenings. Hot tub hookup in place. Shed and outbuilding provide endless hobby, farm, or craft options. The 30 x 36 metal building has a large open space with multiple smaller rooms with electric and heat. Working at home? Talkie WiFi is available. RV hook-up at both the house and the outbuilding. Underground dog fence and 2 collars will stay . Metal building is in good shape but being sold “as is”. Abandoned underground oil tank on site. This type of property does not often come to market. DONT MISS IT! Home is on a shared R-O-W. No drive-bys. OPEN HOUSE SUNDAY THE 24TH 1- 3 PM. Pets on site so please provide as much notice for showings as possible. 3 Beds ⋅ 2 Baths (Pics are from a prior listing. New pics on the way) Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you name it. 15 acres, with small pond and open areas for your animals, sports field, fire pit or huge gardens. Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or biking trail and hunting possible all part of what makes this place a dream come true. In the home enjoy large family room with propane fireplace, beautiful kitchen with stainless steel appliances and granite counters. Custom cabinets and built-ins, wood, laminate, and tile floors throughout. Entry level and second level bedrooms. Ready to relax head to the screened porch for quiet evenings. Hot tub hookup in place. Shed and outbuilding provide endless hobby, farm, or craft options. The 30 x 36 metal building has a large open space with multiple smaller rooms with electric and heat. Working at home? Talkie WiFi is available. RV hook-up at both the house and the outbuilding. Underground dog fence and 2 collars will stay . Metal building is in good shape but being sold “as is”. Abandoned underground oil tank on site. This type of property does not often come to market. DONT MISS IT! Home is on a shared R-O-W. No drive-bys. OPEN HOUSE SUNDAY THE 24TH 1- 3 PM. Pets on site so please provide as much notice for showings as possible. 118 Westwood Ln, Chestertown Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact: (800) 383-3535
$540,000 Modern Cape Cod style home in peaceful Orchard Hill sitting on 1.89 acres. Interior boasts vaulted ceilings, ground floor primary bedroom , upgraded kitchen offering granite counter tops, quality stainless appliances, island with gas cooktop and built-in wine refrigerator. The Primary bedroom includes a luxury primary bath with a jetted tub and stylish tile shower with glass doors. The openness of the mail level is conducive to entertaining and includes the convenience of a bar with sink. Outdoor space is abundant and includes a screened porch, large composite deck with retractable canopy, gazebo and beautiful English cottage gardens which include many native plants. This property provides ample space for gardening or play and offers a peaceful backdrop backing to trees and farmland. It's a MUST SEE. 3 Beds ⋅ 3 Baths Modern Cape Cod style home in peaceful Orchard Hill sitting on 1.89 acres. Interior boasts vaulted ceilings, ground floor primary bedroom , upgraded kitchen offering granite counter tops, quality stainless appliances, island with gas cooktop and built-in wine refrigerator. The Primary bedroom includes a luxury primary bath with a jetted tub and stylish tile shower with glass doors. The openness of the mail level is conducive to entertaining and includes the convenience of a bar with sink. Outdoor space is abundant and includes a screened porch, large composite deck with retractable canopy, gazebo and beautiful English cottage gardens which include many native plants. This property provides ample space for gardening or play and offers a peaceful backdrop backing to trees and farmland. It's a MUST SEE. 8757 Orchard Dr, Chestertown Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
$520,000 Discovery your sanctuary on this 6 plus acre property, nestled on the outskirts of Chestertown. The property houses an abundance of wildlife such as deer, turkey, fox, and ducks! You might even find a beaver swimming up the creek. Thoughtfully updated, you won’t want to miss this a little over 1600 sq ft 3 bedroom 3 bath home, which includes two en-suites. A 420 sq. ft addition was completed in 2023, which boasts white oak flooring, high end bathroom finishes and a tranquil master bedroom. Additionally, you will find a brand-new kitchen where modern elegance meets farmhouse charm. Adorned with shiplap accents, a farmhouse sink, and stunning two-tone cabinets, this culinary haven is as stylish as it is functional, including new stainless steel appliances. It doesn’t stop there, the remainder of the home includes refinished hardwood floors, new tile throughout the kitchen and hall bathroom, all new baseboard, window and door trim, updated light fixtures as well as finishes. In 2022, the exterior received a complete makeover with a new deck, sheathing, vinyl siding, upgraded soffits, and exterior doors, while brand new Jeld Wen windows adorned with sleek black trim enhance both style and functionality. New insulation was added to the attic to create an efficient home. Utilize the unfinished basement (1200 sq ft), located within the footprint of the original home, for plenty of storage space to accommodate your belongings and keep your living areas clutter-free. Stay connected to the world with access to two fiber internet services, ThinkBig and Talkie. Whether you're working from home or streaming your favorite shows, lightning-fast connectivity is always at your fingertips. Centrally located, this property is just 42 miles to Dover, Delaware, and 53 miles to Annapolis, Maryland. For boat enthusiasts, it's a mere 4 miles to Jellyfish Joel's or Tolchester Beach, and less than 10 miles to Rock Hall, providing easy access to some of the area's most popular waterfront destinations. 3 Beds ⋅ 3 Baths Discovery your sanctuary on this 6 plus acre property, nestled on the outskirts of Chestertown. The property houses an abundance of wildlife such as deer, turkey, fox, and ducks! You might even find a beaver swimming up the creek. Thoughtfully updated, you won’t want to miss this a little over 1600 sq ft 3 bedroom 3 bath home, which includes two en-suites. A 420 sq. ft addition was completed in 2023, which boasts white oak flooring, high end bathroom finishes and a tranquil master bedroom. Additionally, you will find a brand-new kitchen where modern elegance meets farmhouse charm. Adorned with shiplap accents, a farmhouse sink, and stunning two-tone cabinets, this culinary haven is as stylish as it is functional, including new stainless steel appliances. It doesn’t stop there, the remainder of the home includes refinished hardwood floors, new tile throughout the kitchen and hall bathroom, all new baseboard, window and door trim, updated light fixtures as well as finishes. In 2022, the exterior received a complete makeover with a new deck, sheathing, vinyl siding, upgraded soffits, and exterior doors, while brand new Jeld Wen windows adorned with sleek black trim enhance both style and functionality. New insulation was added to the attic to create an efficient home. Utilize the unfinished basement (1200 sq ft), located within the footprint of the original home, for plenty of storage space to accommodate your belongings and keep your living areas clutter-free. Stay connected to the world with access to two fiber internet services, ThinkBig and Talkie. Whether you're working from home or streaming your favorite shows, lightning-fast connectivity is always at your fingertips. Centrally located, this property is just 42 miles to Dover, Delaware, and 53 miles to Annapolis, Maryland. For boat enthusiasts, it's a mere 4 miles to Jellyfish Joel's or Tolchester Beach, and less than 10 miles to Rock Hall, providing easy access to some of the area's most popular waterfront destinations. 9816 Fairlee Road, Chestertown Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900
$519,900 Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. This parcel offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. This parcel offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Truslow Farm Ln Unit #LOT 3, Chestertown Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
$519,900 Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. This parcel offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. This parcel offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Truslow Farm Ln Unit #LOT 4, Chestertown Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
$519,900 Discover the opportunity to claim your own piece of history with this 2.3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, these parcels represent a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. These parcels offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Discover the opportunity to claim your own piece of history with this 2.3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, these parcels represent a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. These parcels offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Truslow Farm Ln Unit #LOT 2, Chestertown Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
$497,000 Located on a highly traversed main road, this unassuming yet strategically located commercial office building offers a blend of functionality and convenience--reflected in the interior's generously sized offices and a conference room. The building's practicality extends to its exterior with room for ample parking and opportunities to install suitable landscaping. This property is all about getting the job done efficiently while maintaining a prominent presence on a main road for visibility and accessibility, making it an excellent choice for businesses of all types. Located on a highly traversed main road, this unassuming yet strategically located commercial office building offers a blend of functionality and convenience--reflected in the interior's generously sized offices and a conference room. The building's practicality extends to its exterior with room for ample parking and opportunities to install suitable landscaping. This property is all about getting the job done efficiently while maintaining a prominent presence on a main road for visibility and accessibility, making it an excellent choice for businesses of all types. 830 High St, Chestertown Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440
$449,000 (3 rooms still being renovated - pictures to come March 17th. Living room, laundry and front sitting room) Welcome to this cozy 3 bedroom, 1 bath completely remodeled home with views of the Chester River and a lovely yard full of mature gardens. New heating/air conditioning mini splits, new siding, windows and doors. New electric tankless hot water heater, new washer & dryer, LVP floors, new carpet, new stainless-steel appliances, fresh paint, plantation shutters and new window treatments throughout, electric with solar panels to help absorb energy costs. New front steps, seamless gutters and new lighting. Located in Queen Anne's County, Chestertown MD on a dead-end dirt road. Home has a 12 x 16 treated lumber deck at rear entry and a 10 x 12 shed matching siding, new windows, and new tin roof Enjoy peaceful days and night as this home is located on a no outlet dirt road. The yard is abundant with flowering trees, shrubs and flowers to enjoy your morning coffee or evening sunsets. Annual events include the Chestertown Tea Party and Tall Ship Down Rigging Weekend. Residents and visitors alike enjoy the vibrant arts community, restaurants, shopping, the Saturday Farmers/Artisan Market, parks, rails-to-trails and water activities. Just 25 minutes to the Bay bridge or Middletown, De. Must See! 3 Beds ⋅ 1 Baths (3 rooms still being renovated - pictures to come March 17th. Living room, laundry and front sitting room) Welcome to this cozy 3 bedroom, 1 bath completely remodeled home with views of the Chester River and a lovely yard full of mature gardens. New heating/air conditioning mini splits, new siding, windows and doors. New electric tankless hot water heater, new washer & dryer, LVP floors, new carpet, new stainless-steel appliances, fresh paint, plantation shutters and new window treatments throughout, electric with solar panels to help absorb energy costs. New front steps, seamless gutters and new lighting. Located in Queen Anne's County, Chestertown MD on a dead-end dirt road. Home has a 12 x 16 treated lumber deck at rear entry and a 10 x 12 shed matching siding, new windows, and new tin roof Enjoy peaceful days and night as this home is located on a no outlet dirt road. The yard is abundant with flowering trees, shrubs and flowers to enjoy your morning coffee or evening sunsets. Annual events include the Chestertown Tea Party and Tall Ship Down Rigging Weekend. Residents and visitors alike enjoy the vibrant arts community, restaurants, shopping, the Saturday Farmers/Artisan Market, parks, rails-to-trails and water activities. Just 25 minutes to the Bay bridge or Middletown, De. Must See! 134 Char Nor Manor Blvd, Chestertown Listing courtesy of Taylor Properties. Contact:
$425,000 Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. This parcel offers the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. Discover the opportunity to claim your own piece of history with this 3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, this parcel represents a few of the last untouched waterfront canvases, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. This parcel offers the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time. 210 Truslow Farm Ln, Chestertown Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
$419,900 Currently undergoing construction, this brand new home offers the opportunity to select your preferred colors for the granite kitchen countertops, vinyl flooring, and paint, but you have to act fast! Anticipated completion by May 1st, this 3-bedroom, 2.5-bathroom Cape Cod boasts water views of the Chester River. Featuring an open-concept layout, stainless steel appliances, and a main-level master with walk-in closet, and ensuite. Upstairs, discover two generously sized bedrooms accompanied by an additional full bathroom. Located at the end of a quiet, private street. Don't delay and miss the opportunity to put your personal touches on it! 3 Beds ⋅ 3 Baths Currently undergoing construction, this brand new home offers the opportunity to select your preferred colors for the granite kitchen countertops, vinyl flooring, and paint, but you have to act fast! Anticipated completion by May 1st, this 3-bedroom, 2.5-bathroom Cape Cod boasts water views of the Chester River. Featuring an open-concept layout, stainless steel appliances, and a main-level master with walk-in closet, and ensuite. Upstairs, discover two generously sized bedrooms accompanied by an additional full bathroom. Located at the end of a quiet, private street. Don't delay and miss the opportunity to put your personal touches on it! 481 Pear Tree Point Rd, Chestertown Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$415,000 Price Improvement! Don't miss your chance to own this charming rancher located in the sought-after community of The Grove. With over 2200+ square feet this property offers the perfect blend of comfort and privacy. Three bedrooms, two bathrooms, and an open floor plan create a bright and inviting space. The well-designed layout ensures privacy with the primary suite and en-suite cleverly separated. The modern kitchen is perfect for culinary adventures. The attached 428ft garage, equipped with a generator, has been converted to add additional living space perfect for an entertainment, theatre, or game room. Situated on 1.23 acres, partially fenced for privacy, this home is nestled in a quiet neighborhood on a cul-de-sac within the esteemed Queen Anne's County school district. Fenced lot offers additional storage with a 25x32ft detached garage/pole barn perfect for any enthusiastic hobbyist! Restaurants, beach, and marinas are all within 2 miles, offering plenty of sunshine fun! Within Queen Anne County school district and perfectly positioned just a few short miles from Centreville or Downtown Chestertown showcasing festivals, farmer markets, restaurants, walking trails, parks, and artisan stores galore! Minutes to 301 for easy commuting to Annapolis, Baltimore, DC or Delaware. 3 Beds ⋅ 2 Baths Price Improvement! Don't miss your chance to own this charming rancher located in the sought-after community of The Grove. With over 2200+ square feet this property offers the perfect blend of comfort and privacy. Three bedrooms, two bathrooms, and an open floor plan create a bright and inviting space. The well-designed layout ensures privacy with the primary suite and en-suite cleverly separated. The modern kitchen is perfect for culinary adventures. The attached 428ft garage, equipped with a generator, has been converted to add additional living space perfect for an entertainment, theatre, or game room. Situated on 1.23 acres, partially fenced for privacy, this home is nestled in a quiet neighborhood on a cul-de-sac within the esteemed Queen Anne's County school district. Fenced lot offers additional storage with a 25x32ft detached garage/pole barn perfect for any enthusiastic hobbyist! Restaurants, beach, and marinas are all within 2 miles, offering plenty of sunshine fun! Within Queen Anne County school district and perfectly positioned just a few short miles from Centreville or Downtown Chestertown showcasing festivals, farmer markets, restaurants, walking trails, parks, and artisan stores galore! Minutes to 301 for easy commuting to Annapolis, Baltimore, DC or Delaware. 209 Myers Rd, Chestertown Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$385,500 This is truly a unique find. With over 3 acres of room to play, hunt, ride 4 wheelers, have critters, this property won't last long. Owner has wonderfully updated almost everything about this house and there is home warranty for peace of mind. Relax in the morning on the front porch and watch nature from every window. Gorgeous spacious kitchen with granite counters and including an eat in one that will seat at least four. All brand new appliances convey including washer and dryer. Cozy up by the wood burning fireplace or explore your little piece of heaven. This property used to be 2 lots and county says its zoned for several lots that can be potentially taken off. Explore the possibilities. Shown by Appointment only. 3 Beds ⋅ 2 Baths This is truly a unique find. With over 3 acres of room to play, hunt, ride 4 wheelers, have critters, this property won't last long. Owner has wonderfully updated almost everything about this house and there is home warranty for peace of mind. Relax in the morning on the front porch and watch nature from every window. Gorgeous spacious kitchen with granite counters and including an eat in one that will seat at least four. All brand new appliances convey including washer and dryer. Cozy up by the wood burning fireplace or explore your little piece of heaven. This property used to be 2 lots and county says its zoned for several lots that can be potentially taken off. Explore the possibilities. Shown by Appointment only. 9062 Fairlee Rd, Chestertown Listing courtesy of Taylor Properties. Contact:
$385,000 Embrace the walkable lifestyle of Chestertown in this completely renovated downtown gem from 1900. Experience both historic charm and modern amenities as this home has all brand new plumbing, electrical, insulation, HVAC, and roofing. Make the most of one floor living with the beautifully designed first floor owner's suite. The ensuite owner's bathroom comes with a tastefully tiled walk-in shower. Double doors open right from the suite onto the covered side porch that wraps around to a private back deck. An all new kitchen is awaiting your culinary pursuits while the open floor plan drawing you to the living room remains flooded with natural light from the tall historic windows. The second floor has two generous sized bedrooms and another new full bathroom. The front bedroom has a staircase up the finished third floor hobby room. The rear yard is fenced, shaded and ready for your next cookout. Off street parking is another added bonus to this property. Enjoy the perfect balance of historic and upgraded with this catch just a few blocks from Chestertown's shops, culture and waterfront. 3 Beds ⋅ 2 Baths Embrace the walkable lifestyle of Chestertown in this completely renovated downtown gem from 1900. Experience both historic charm and modern amenities as this home has all brand new plumbing, electrical, insulation, HVAC, and roofing. Make the most of one floor living with the beautifully designed first floor owner's suite. The ensuite owner's bathroom comes with a tastefully tiled walk-in shower. Double doors open right from the suite onto the covered side porch that wraps around to a private back deck. An all new kitchen is awaiting your culinary pursuits while the open floor plan drawing you to the living room remains flooded with natural light from the tall historic windows. The second floor has two generous sized bedrooms and another new full bathroom. The front bedroom has a staircase up the finished third floor hobby room. The rear yard is fenced, shaded and ready for your next cookout. Off street parking is another added bonus to this property. Enjoy the perfect balance of historic and upgraded with this catch just a few blocks from Chestertown's shops, culture and waterfront. 529 Cannon St, Chestertown Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
$340,000 Be sure to check out the photos - this home has real charm and character! This well-maintained house has been home to the same family since 1975: blacktopped driveway resealed in 2022, new roof 2017, new well 2016, quarterly Pest Service and mature landscaping with a fenced backyard. New washer and dryer and a full tank of propane for use of the attractive oak fireplace. Both bathrooms completely updated 2024. Both large upstairs bedrooms have double windows which allow for maximum light during the day. The property sits on four lots for a total of .69 acres. The quiet community of Chester Harbor has a voluntary HOA which allows for Chester River water access and use of the community area located at the end of Fairview Drive. Round Top Park is close by - ball courts, playground and a pavilion. Close to historic Chestertown and just 45 minutes to Middletown and tax-free shopping! 3 Beds ⋅ 2 Baths Be sure to check out the photos - this home has real charm and character! This well-maintained house has been home to the same family since 1975: blacktopped driveway resealed in 2022, new roof 2017, new well 2016, quarterly Pest Service and mature landscaping with a fenced backyard. New washer and dryer and a full tank of propane for use of the attractive oak fireplace. Both bathrooms completely updated 2024. Both large upstairs bedrooms have double windows which allow for maximum light during the day. The property sits on four lots for a total of .69 acres. The quiet community of Chester Harbor has a voluntary HOA which allows for Chester River water access and use of the community area located at the end of Fairview Drive. Round Top Park is close by - ball courts, playground and a pavilion. Close to historic Chestertown and just 45 minutes to Middletown and tax-free shopping! 707 Round Top Rd, Chestertown Listing courtesy of The Hogans Agency Inc.. Contact: (410) 778-1665
$299,900 Come by this AWESOME, RENOVATED Rancher in the WATERFRONT Community of Chesapeake Landing is Chestertown. This beautifully renovated single level home is ready for it's new owner today! This home has been carefully renovated in the last few months, including new luxury vinyl plank flooring, new kitchen with white shaker cabinets, granite countertops, new bathrooms, new appliances and much more! Special financing is available for this home making it more afforable to own a home than rent one! 4 Beds ⋅ 2 Baths Come by this AWESOME, RENOVATED Rancher in the WATERFRONT Community of Chesapeake Landing is Chestertown. This beautifully renovated single level home is ready for it's new owner today! This home has been carefully renovated in the last few months, including new luxury vinyl plank flooring, new kitchen with white shaker cabinets, granite countertops, new bathrooms, new appliances and much more! Special financing is available for this home making it more afforable to own a home than rent one! 10605 Tonopah Rd, Chestertown Listing courtesy of RE/MAX Executive. Contact: (443) 292-9250