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PRICE IMPROVEMENT!! Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas. Call to set up an appointment!

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$275,000

**NEW PRICE! MOTIVATED SELLER WILLING TO CONSIDER BUYER CLOSING COST ASSISTANCE OR INTEREST RATE BUYDOWN!** Here's an opportunity worth a second look! With a fresh price improvement and a seller ready to make a move, now is the time to explore the possibilities. Imagine settling into your new home before the holidays and potentially making your first mortgage payment in 2027! This charming Chestertown rancher offers bright, updated interiors, comfortable single-level living, a spacious corner lot, newer paver patio, fenced backyard and no community HOA. Whether you're purchasing your first home, looking to simplify or searching for an easy-to-maintain property, there's plenty to love here. Schedule your tour, bring your offer and let's make a move!

**NEW PRICE! MOTIVATED SELLER WILLING TO CONSIDER BUYER CLOSING COST ASSISTANCE OR INTEREST RATE BUYDOWN!** Here's an opportunity worth a second look! With a fresh price improvement and a seller ready to make a move, now is the time to explore the possibilities. Imagine settling into your new home before the holidays and potentially making your first mortgage payment in 2027! This charming Chestertown rancher offers bright, updated interiors, comfortable single-level living, a spacious corner lot, newer paver patio, fenced backyard and no community HOA. Whether you're purchasing your first home, looking to simplify or searching for an easy-to-maintain property, there's plenty to love here. Schedule your tour, bring your offer and let's make a move!

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

$359,000

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

374 Hurtt Ave, Millington

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

$270,000

Recently Renovated Rancher with Inviting Outdoor Living! Welcome to 25213 Porters Grove Road in Worton, Maryland! This beautifully refreshed 3-bedroom, 2-full-bath ranch-style home offers the perfect combination of modern updates, comfortable living, and inviting outdoor space. With its open-concept layout, recent renovations, and spacious yard, this home is ready for its next chapter! Step inside and enjoy a bright, welcoming living area that flows seamlessly into the eat-in kitchen, creating an ideal setting for everyday living and entertaining. Recent updates, including carpeting and tile finishes in the kitchen and bathrooms, add a fresh touch throughout the home. The thoughtfully designed floor plan makes excellent use of the space while maintaining an open and inviting atmosphere. The home features three comfortably sized bedrooms, including a primary bedroom with its own attached full bathroom, offering added privacy and convenience. A second full bathroom provides functionality for guests and everyday living. Step outside and discover even more to love! The generous backyard and side yard offer plenty of green space to enjoy outdoor activities, gardening, entertaining, or simply relaxing in the fresh air. The patio creates a wonderful spot for outdoor dining, while the fire pit provides the perfect gathering place for evenings under the stars. Whether you're hosting a weekend cookout or enjoying a quiet afternoon outdoors, this property offers space to make lasting memories. A large driveway provides convenient off-street parking with room for multiple vehicles. Located in Worton, Maryland, with convenient access to nearby Chestertown and the surrounding Kent County area, this home offers an appealing blend of comfort, practicality, and outdoor enjoyment. With recent improvements, an open floor plan, three bedrooms, two full bathrooms, and inviting outdoor living areas, this property is an opportunity you won't want to miss. Schedule your private tour today and see all that 25213 Porters Grove Road has to offer!

Recently Renovated Rancher with Inviting Outdoor Living! Welcome to 25213 Porters Grove Road in Worton, Maryland! This beautifully refreshed 3-bedroom, 2-full-bath ranch-style home offers the perfect combination of modern updates, comfortable living, and inviting outdoor space. With its open-concept layout, recent renovations, and spacious yard, this home is ready for its next chapter! Step inside and enjoy a bright, welcoming living area that flows seamlessly into the eat-in kitchen, creating an ideal setting for everyday living and entertaining. Recent updates, including carpeting and tile finishes in the kitchen and bathrooms, add a fresh touch throughout the home. The thoughtfully designed floor plan makes excellent use of the space while maintaining an open and inviting atmosphere. The home features three comfortably sized bedrooms, including a primary bedroom with its own attached full bathroom, offering added privacy and convenience. A second full bathroom provides functionality for guests and everyday living. Step outside and discover even more to love! The generous backyard and side yard offer plenty of green space to enjoy outdoor activities, gardening, entertaining, or simply relaxing in the fresh air. The patio creates a wonderful spot for outdoor dining, while the fire pit provides the perfect gathering place for evenings under the stars. Whether you're hosting a weekend cookout or enjoying a quiet afternoon outdoors, this property offers space to make lasting memories. A large driveway provides convenient off-street parking with room for multiple vehicles. Located in Worton, Maryland, with convenient access to nearby Chestertown and the surrounding Kent County area, this home offers an appealing blend of comfort, practicality, and outdoor enjoyment. With recent improvements, an open floor plan, three bedrooms, two full bathrooms, and inviting outdoor living areas, this property is an opportunity you won't want to miss. Schedule your private tour today and see all that 25213 Porters Grove Road has to offer!

25213 Porters Grove Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact:

$339,000

Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - year round or as a well loved second home! Many furnishings can be included! Carefree living in a completely renovated complex with so much to offer - charming updated condo with main floor living and access to a saltwater pool, sandy beach with picnic area, bathhouse, and boat ramp plus a deeded 30' boat slip with an 8,000 lb lift with new motor, new cables, remote control and dock box. The boat dock is accessed via the private gated dock on the Sassafras. This home includes a lovely expansive covered porch and large protected storage area underneath for all the toys! Historic Chestertown and the waterman's town of Rock Hall are just short drives away with a variety of dining and shopping options in both of these waterfront towns. There is a lot of value to be found here for a very reasonable price!

Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - year round or as a well loved second home! Many furnishings can be included! Carefree living in a completely renovated complex with so much to offer - charming updated condo with main floor living and access to a saltwater pool, sandy beach with picnic area, bathhouse, and boat ramp plus a deeded 30' boat slip with an 8,000 lb lift with new motor, new cables, remote control and dock box. The boat dock is accessed via the private gated dock on the Sassafras. This home includes a lovely expansive covered porch and large protected storage area underneath for all the toys! Historic Chestertown and the waterman's town of Rock Hall are just short drives away with a variety of dining and shopping options in both of these waterfront towns. There is a lot of value to be found here for a very reasonable price!

1 Bayview Rd Unit 19A, Betterton

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

$299,000

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

11037 Bottom Rd, Worton

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

$370,000

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

4 Beds ⋅ 3 Baths

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

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

$369,900

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

13831 Augustine Herman Hwy, Galena

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

$259,000

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

115 Chester Arms Dr, Chestertown

Listing courtesy of Samson Properties. Contact:

$359,000

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

101 S College Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,900

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

5 Beds ⋅ 3 Baths

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

$334,900

Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main floor offers a large entry with a view of the living room, dining room, stunning kitchen, and a beautiful open wood staircase. The stunning kitchen boasts a vaulted ceiling, ample cabinets finished with crown moldings, stainless steel appliances (including an electric cooktop and lower wall oven), granite countertops, and a double stainless sink. Just off the entryway is a full bath with laundry. On the second floor are two sizable secondary bedrooms, a larger primary bedroom with access to one of the secondary bedrooms, and a full bath featuring a walk-in shower with a spa feature. From the kitchen's sliding doors, step onto a spacious wood deck overlooking the semi-fenced yard, which offers green space, numerous possibilities, and a detached garage. This move-in-ready home is ideal for any new homeowner and is located near shopping, restaurants and commuter routes.

Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main floor offers a large entry with a view of the living room, dining room, stunning kitchen, and a beautiful open wood staircase. The stunning kitchen boasts a vaulted ceiling, ample cabinets finished with crown moldings, stainless steel appliances (including an electric cooktop and lower wall oven), granite countertops, and a double stainless sink. Just off the entryway is a full bath with laundry. On the second floor are two sizable secondary bedrooms, a larger primary bedroom with access to one of the secondary bedrooms, and a full bath featuring a walk-in shower with a spa feature. From the kitchen's sliding doors, step onto a spacious wood deck overlooking the semi-fenced yard, which offers green space, numerous possibilities, and a detached garage. This move-in-ready home is ideal for any new homeowner and is located near shopping, restaurants and commuter routes.

5862 N Main St, Rock Hall

Listing courtesy of LPT Realty, LLC. Contact:

$267,000

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$330,000

Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops and sinks add an elegant modern touch. Two plus bedrooms and a custom built sleeping loft provide enough room for occasional guests. Fixed stairs to the attic offer room to expand. The Chesapeake Bay is a short walk to the end of the road where you can launch a kayak or just enjoy the water views. Just outside the quaint town of Rock Hall, this charming cottage would make a great vacation or retirement home.

Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops and sinks add an elegant modern touch. Two plus bedrooms and a custom built sleeping loft provide enough room for occasional guests. Fixed stairs to the attic offer room to expand. The Chesapeake Bay is a short walk to the end of the road where you can launch a kayak or just enjoy the water views. Just outside the quaint town of Rock Hall, this charming cottage would make a great vacation or retirement home.

21352 Allens Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$259,900

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

*Open Every Tuesdy and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

115 Metcalf Rd, Chestertown

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

$264,900

*Open Every Tuesday and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations.

*Open Every Tuesday and Thursday from 6 to 7pm* Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations.

121 Metcalf Rd, Chestertown

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

$199,000

Unique opportunity to restore and customize the historic former "Rock Hall Shirt Factory!" This 5,558± sq. ft. building is situated on a 0.31± acre in-town lot and offers endless potential for investors, developers, or buyers looking for a one-of-a-kind project. The interior has been framed and studded for rooms, providing a head start on the renovation process while allowing you to complete the layout to suit your vision. Zoned R-3 High Density Residential, the property may offer the potential for multiple apartments or conversion into duplex or triplex units, subject to Town of Rock Hall approval and all applicable zoning and building requirements. The property features two separate driveways, a one-car garage, and all remaining contents will convey with the sale, potentially including valuable construction materials to assist with completing the project. Conveniently located just a short walk from Rock Hall's charming Main Street, you'll enjoy easy access to local shops, restaurants, the harbor, and community events. Bring your imagination and transform this historic property into something truly special!

5804 Downey Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$334,900

321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'll find a formal living room, a dining area, and a fully equipped kitchen with stainless steel appliances, along with a nicely sized island that offers additional space for dining. The main level also includes a laundry room with stackable washer & dryer included. Down the spiral staircase to the ground level you'll discover a one-car garage and a full unfinished basement with daylight windows - perfect for extra storage or future possibilities. Situated on a level rectangular .23 acre lot, this property offers both comfort and potential. Settlement date is negotiable and we kindly ask for a 1 hour prior notice for all showings. This home DOES HAVE an FHA assumable mortgage.

321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'll find a formal living room, a dining area, and a fully equipped kitchen with stainless steel appliances, along with a nicely sized island that offers additional space for dining. The main level also includes a laundry room with stackable washer & dryer included. Down the spiral staircase to the ground level you'll discover a one-car garage and a full unfinished basement with daylight windows - perfect for extra storage or future possibilities. Situated on a level rectangular .23 acre lot, this property offers both comfort and potential. Settlement date is negotiable and we kindly ask for a 1 hour prior notice for all showings. This home DOES HAVE an FHA assumable mortgage.

321 West St, Millington

Listing courtesy of RE/MAX Associates - Newark. Contact:

$289,000

Bring your vision to this rare 15-acre property offering privacy, natural beauty, and endless possibilities. Mostly wooded with a picturesque pond, this property is an ideal setting for those seeking a private retreat, recreational getaway, or future homesite. An original structure dating back to 1980 remains on the property and includes a full basement. The condition existing home is believed unknown and is being sold strictly as-is. Do not enter any structures on the property. Whether you dream of restoring or rebuilding within the existing footprint (subject to county approvals), creating a hunting or fishing retreat, harvesting the mature hardwoods, or simply enjoying the peace and quiet of nature, this property offers exceptional potential. A perfect place to live, play, or both, with convenient access to Route 301 for an easy commute to Maryland, Delaware, and beyond. Buyer to verify all zoning, land use, and building possibilities.

31001 Chesterville Bridge Rd, Millington

Listing courtesy of RE/MAX Executive. Contact:

$313,500

SELLER IS OFFERING UP TO $7,500 TOWARDS A 2-1 RATE BUY DOWN TO LOWER YOUR MONTHLY MORTGAGE PAYMENT OR FUNDS TOWARDS CLOSING COSTS SO YOU BRING LESS MONEY TO THE CLOSING TABLE, WITH A FULL PRICED OFFER! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a vacation home, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. In addition, this property has public water and sewer. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

SELLER IS OFFERING UP TO $7,500 TOWARDS A 2-1 RATE BUY DOWN TO LOWER YOUR MONTHLY MORTGAGE PAYMENT OR FUNDS TOWARDS CLOSING COSTS SO YOU BRING LESS MONEY TO THE CLOSING TABLE, WITH A FULL PRICED OFFER! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a vacation home, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. In addition, this property has public water and sewer. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

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

$375,000

Sweet corner property in downtown Rock Hall, right on the 4th of July parade route! Just two blocks from the Rock Hall Harbor/ Chesapeake Bay. A welcoming home with a spacious kitchen and formal dining room, or enjoy meals outside in the fenced-in back yard! The large living room has hardwood floors and a wood stove for cozy winter nights. This home features a hard to find first-floor primary bedroom! Upstairs offers two additional bedrooms, a full bath, and an additional office or activity room. The home is situated on a large corner lot, set back from Main St., offering privacy and nice yard space. The charming garage with a loft is a great space for storage or a workshop. Close to all Rock Hall has to offer: marinas, shops, restaurants, and the Chesapeake Bay! This popular vacation rental could continue as an income producer but would also make a fantastic full-time residence. Being sold turn-key, just unpack your bags and enjoy. The homes hot water heat has been updated, zoned to both floors. Tankless hot water heater.

Sweet corner property in downtown Rock Hall, right on the 4th of July parade route! Just two blocks from the Rock Hall Harbor/ Chesapeake Bay. A welcoming home with a spacious kitchen and formal dining room, or enjoy meals outside in the fenced-in back yard! The large living room has hardwood floors and a wood stove for cozy winter nights. This home features a hard to find first-floor primary bedroom! Upstairs offers two additional bedrooms, a full bath, and an additional office or activity room. The home is situated on a large corner lot, set back from Main St., offering privacy and nice yard space. The charming garage with a loft is a great space for storage or a workshop. Close to all Rock Hall has to offer: marinas, shops, restaurants, and the Chesapeake Bay! This popular vacation rental could continue as an income producer but would also make a fantastic full-time residence. Being sold turn-key, just unpack your bags and enjoy. The homes hot water heat has been updated, zoned to both floors. Tankless hot water heater.

5686 S Main St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$325,000

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

896 Washington Ave, Chestertown

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

$310,000

Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large back porch for entertaining and a large plot of land to build on if you wish. Experience the charm of this beautifully renovated colonial home in the heart of Kent County, where classic elegance meets modern luxury. Set on a generous 0.21-acre lot, this detached residence has undergone a major renovation in 2026, ensuring a seamless blend of timeless design and contemporary comforts. Step inside to discover a warm and inviting atmosphere, accentuated by high-end finishes throughout. The spacious layout features two well-appointed bedrooms and two full bathrooms, providing ample space for relaxation and rejuvenation. The heart of the home boasts a state-of-the-art kitchen equipped with a built-in microwave, perfect for culinary enthusiasts and entertaining guests. Natural light floods the interior, highlighting the exquisite craftsmanship defines this property. The exterior, adorned with durable vinyl siding, complements the classic colonial architecture, while the crushed stone driveway offers both functionality and curb appeal. Enjoy the tranquility of your surroundings in this peaceful neighborhood, where you can unwind on your private lot, free from the hustle and bustle of city life. With parking for up to three vehicles, convenience is at your fingertips. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and sophistication. Embrace the opportunity to make this exquisite property your own and indulge in the luxury of modern living in a historic setting. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all.

Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large back porch for entertaining and a large plot of land to build on if you wish. Experience the charm of this beautifully renovated colonial home in the heart of Kent County, where classic elegance meets modern luxury. Set on a generous 0.21-acre lot, this detached residence has undergone a major renovation in 2026, ensuring a seamless blend of timeless design and contemporary comforts. Step inside to discover a warm and inviting atmosphere, accentuated by high-end finishes throughout. The spacious layout features two well-appointed bedrooms and two full bathrooms, providing ample space for relaxation and rejuvenation. The heart of the home boasts a state-of-the-art kitchen equipped with a built-in microwave, perfect for culinary enthusiasts and entertaining guests. Natural light floods the interior, highlighting the exquisite craftsmanship defines this property. The exterior, adorned with durable vinyl siding, complements the classic colonial architecture, while the crushed stone driveway offers both functionality and curb appeal. Enjoy the tranquility of your surroundings in this peaceful neighborhood, where you can unwind on your private lot, free from the hustle and bustle of city life. With parking for up to three vehicles, convenience is at your fingertips. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and sophistication. Embrace the opportunity to make this exquisite property your own and indulge in the luxury of modern living in a historic setting. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all.

21232 Rock Hall Ave, Rock Hall

Listing courtesy of RE/MAX Advantage Realty. Contact:

$350,000

Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor bedroom and full bathroom, plus two additional bedrooms and a full bath on the second floor. There's a walk-up attic for additional storage, shed in the yard, laundry and utility room off the kitchen. Many updates have been made throughout the years, such as the addition of a copper roof on the front porch, updated bathrooms, flooring, and updated lighting. Recent updates include the home's heating system. Don't miss this downtown gem!

Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor bedroom and full bathroom, plus two additional bedrooms and a full bath on the second floor. There's a walk-up attic for additional storage, shed in the yard, laundry and utility room off the kitchen. Many updates have been made throughout the years, such as the addition of a copper roof on the front porch, updated bathrooms, flooring, and updated lighting. Recent updates include the home's heating system. Don't miss this downtown gem!

21384 E Sharp St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$395,000

Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

3 Beds ⋅ 3 Baths

Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

21712 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

11989 Augustine Herman Hwy, Kennedyville

$245,000

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

2 Baths

Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$289,000

Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

4818 Piney Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$239,900

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!