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ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/22/2026, 10:00 AM. Bidding ends 10/26/2026, 1:30 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Maryland’s Eastern Shore in Kent County, this single-family home offers approximately 1,896 square feet of living area on a 0.51± acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property.

10520 Worton Rd, Worton

Listing courtesy of Ashland Auction Group LLC. Contact:

$90,000

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/22/2026, 10:00 AM. Bidding ends 10/26/2026, 1:40 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Maryland’s Eastern Shore in Kent County, this single-family home offers approximately 1,056 square feet of living area on a 0.46± acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property.

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/22/2026, 10:00 AM. Bidding ends 10/26/2026, 1:40 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Maryland’s Eastern Shore in Kent County, this single-family home offers approximately 1,056 square feet of living area on a 0.46± acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property.

10540 Worton Rd, Worton

Listing courtesy of Ashland Auction Group LLC. 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:

$2,300,000

A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and since renovations has had no vacancies, with solid leases in place. During the renovations every major system in the building was replaced, including new electric service, meters and new wiring throughout, all new plumbing using PEX, new water and septic service lines to the building, new energy efficient water heaters and appliances, rebuilt foundation, new Jeldwen Auralast windows, insulation and air sealing, new roof on rear portions of building (front 50-year cedar roof was replaced in early 2000s), new rear egress, a monitored fire alarm system and much more. Two of the storefronts are rented to a local arts non-profit and a yoga/pilates studio recently moved into the third commercial space. The 5 apartments consist of two 2-bedroom units and three 1-bedroom apartments. The steady income stream from the units is complemented by a generous property tax credit through 2032 (buyer to verify transferability). The property also has a Limited Lead-Free certificate, which requires only an exterior visual inspection every two years, and exempts the owner from MDE registration requirements. Complete income and expense information available after signing a confidentiality agreement. Limited photos posted for tenants' privacy. Contact for a private tour today. Please do not disrupt the businesses, they are tenants and the businesses are not part of the sale.

200 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$565,000

Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful updated granite countertops, a large pantry, kitchen island with seating, and ample cabinet space. From the dining room you can explore the raised deck with a hot tub! Or enjoy meals on the screened porch, finished with water and electricity. This one-level home boasts 3 spacious bedrooms and 2.5 bathrooms. The primary bedroom has a walk-in closet and opens to a sun-filled studio or office space, which has access to the raised deck. There is an attached two-car garage with ample storage space, which could also make a great workshop. Under 15 minutes to downtown Chestertown and less than an hour to Middletown DE. This home is move in ready! The sellers are selling turn-key with contents. Recent updates include: -Refinished hardwood floors throughout home -Granite countertops in kitchen -Updated kitchen appliances -Water treatment system - & more! Solar leased through Tesla

Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful updated granite countertops, a large pantry, kitchen island with seating, and ample cabinet space. From the dining room you can explore the raised deck with a hot tub! Or enjoy meals on the screened porch, finished with water and electricity. This one-level home boasts 3 spacious bedrooms and 2.5 bathrooms. The primary bedroom has a walk-in closet and opens to a sun-filled studio or office space, which has access to the raised deck. There is an attached two-car garage with ample storage space, which could also make a great workshop. Under 15 minutes to downtown Chestertown and less than an hour to Middletown DE. This home is move in ready! The sellers are selling turn-key with contents. Recent updates include: -Refinished hardwood floors throughout home -Granite countertops in kitchen -Updated kitchen appliances -Water treatment system - & more! Solar leased through Tesla

25124 E Kentfield Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$480,000

Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering easy access to waterfront dining, boating, and all the coastal charm Rock Hall has to offer. Relax on the spacious front porch, or entertain on the screened porch, complete with electricity and plenty of space for outdoor dining. Inside, the home seamlessly blends original character with thoughtful modern updates. The large country kitchen retains its classic charm while featuring updated stainless steel appliances. Off of the kitchen you’ll find the formal living and dining rooms, highlighted by beautiful built-in cabinetry and warm original hardwood floors that extend throughout the home. This home offers a first-floor bedroom and an updated full bathroom, offering hard-to-find single-level living. Upstairs there are four additional bedrooms and a second full bathroom, providing plenty of room for family, visitors, or a home office. The large backyard is adjacent to the civic center, providing lots of open space, yet lined with trees for privacy. Filled with warmth, charm, and modern comforts, this beautifully maintained home offers the perfect opportunity to enjoy life in one of Maryland's most beloved waterfront communities. Short distance to Main Street shops, many restaurants, marinas, and the Rock Hall beach. Brand new roof! This home is move in ready! The sellers are selling turn-key with contents.

5 Beds ⋅ 2 Baths

Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering easy access to waterfront dining, boating, and all the coastal charm Rock Hall has to offer. Relax on the spacious front porch, or entertain on the screened porch, complete with electricity and plenty of space for outdoor dining. Inside, the home seamlessly blends original character with thoughtful modern updates. The large country kitchen retains its classic charm while featuring updated stainless steel appliances. Off of the kitchen you’ll find the formal living and dining rooms, highlighted by beautiful built-in cabinetry and warm original hardwood floors that extend throughout the home. This home offers a first-floor bedroom and an updated full bathroom, offering hard-to-find single-level living. Upstairs there are four additional bedrooms and a second full bathroom, providing plenty of room for family, visitors, or a home office. The large backyard is adjacent to the civic center, providing lots of open space, yet lined with trees for privacy. Filled with warmth, charm, and modern comforts, this beautifully maintained home offers the perfect opportunity to enjoy life in one of Maryland's most beloved waterfront communities. Short distance to Main Street shops, many restaurants, marinas, and the Rock Hall beach. Brand new roof! This home is move in ready! The sellers are selling turn-key with contents.

21251 Chesapeake Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,395,000

Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private waterfront oasis and dock. The lower level features a large family room, 2 bedrooms, a full bath and plenty of storage. This home has that unmistakable Eastern Shore feel. You won't want to miss this spectacular property.

4 Beds ⋅ 3 Baths

Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private waterfront oasis and dock. The lower level features a large family room, 2 bedrooms, a full bath and plenty of storage. This home has that unmistakable Eastern Shore feel. You won't want to miss this spectacular property.

12555 Coopers Ln, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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:

$550,000

Rare opportunity to purchase five contiguous parcels totaling 3.765± acres in a prime location near Rock Hall Harbor. Parcel 505 features an older manufactured home situated on approximately 1.27± water-view acres with scenic views of North Point Marina and Rock Hall Harbor. The additional parcels include Parcel 504 (0.853± acres), Parcel 503 (1.04± acres), Parcel 502 (0.258± acres), and Parcel 501 (0.344± acres), offering endless possibilities for expansion, investment, or future development (subject to applicable approvals). The existing home offers over 1,200 square feet of one-level living with three bedrooms and two full baths. While the home is in need of renovation and repairs, it presents an excellent opportunity to create a charming vacation retreat, retirement home, or investment property in a highly desirable waterfront community. The property is being sold As-Is. The lots are cleared and level, providing a fantastic setting to enjoy all that Rock Hall has to offer.

Rare opportunity to purchase five contiguous parcels totaling 3.765± acres in a prime location near Rock Hall Harbor. Parcel 505 features an older manufactured home situated on approximately 1.27± water-view acres with scenic views of North Point Marina and Rock Hall Harbor. The additional parcels include Parcel 504 (0.853± acres), Parcel 503 (1.04± acres), Parcel 502 (0.258± acres), and Parcel 501 (0.344± acres), offering endless possibilities for expansion, investment, or future development (subject to applicable approvals). The existing home offers over 1,200 square feet of one-level living with three bedrooms and two full baths. While the home is in need of renovation and repairs, it presents an excellent opportunity to create a charming vacation retreat, retirement home, or investment property in a highly desirable waterfront community. The property is being sold As-Is. The lots are cleared and level, providing a fantastic setting to enjoy all that Rock Hall has to offer.

5666 Walnut St, 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:

$699,900

Imagine building your dream luxury waterfront home on one of the most spectacular homesites the Chesapeake Bay has to offer. This exceptional waterfront lot boasts breathtaking panoramic views stretching across the Chesapeake Bay to the iconic Bay Bridge and the distant Baltimore skyline, creating an ever-changing backdrop of stunning sunrises, sailboats, and shimmering waterfront vistas. Nestled in the charming waterfront town of Rock Hall, Maryland—known as the "Pearl of the Chesapeake"—this rare property offers the perfect opportunity to design and build a custom coastal retreat tailored to your lifestyle. Whether you envision a sophisticated year-round residence or an unforgettable weekend escape, the possibilities are endless. The convenience of public water and public sewer, making the building process even more attractive while eliminating many of the challenges associated with rural waterfront construction. Spend your days boating, fishing, crabbing, kayaking, or simply relaxing as you take in the peaceful beauty of the Bay. Located just minutes from Rock Hall's marinas, waterfront restaurants, shops, and charming downtown, this remarkable property offers the perfect blend of luxury, convenience, and small-town coastal living. Opportunities like this are incredibly rare—bring your vision and create the waterfront home you've always dreamed of. MOTIVATED SELLER ... BRING ALL OFFERS...

5738 Beach Rd, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

$825,000

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

5 Beds ⋅ 4 Baths

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. 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:

$195,000

15.5 + Acres- Build, Hunt, or Escape! Enjoy approximately 15.5 acres of beautiful open land in a peaceful setting. Previously perced by the prior owner, this property offers incredible potential for your future home, weekend getaway, or private hunting and recreational retreat. Whether you’re looking to build now or invest for the future, this versatile parcel is ready for your vision. A rare opportunity with endless possibilities!

Chestervl-Millington Road, Millington

Listing courtesy of Keller Williams Realty Wilmington. Contact:

$435,000

Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades include all-new appliances (2021), a 12' x 20' shed/workshop (2023), and new HVAC and viny siding (2024). Step outside to a spacious deck overlooking the river and your private dock--perfect for fishing, launching kayaks, or docking a small boat. Conveniently located just 15 minutes from both Chestertown, MD and Middletown, DE, this waterfront retreat offers the ideal blend of comfort, convenience, and outdoor enjoyment. A must-see!

Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades include all-new appliances (2021), a 12' x 20' shed/workshop (2023), and new HVAC and viny siding (2024). Step outside to a spacious deck overlooking the river and your private dock--perfect for fishing, launching kayaks, or docking a small boat. Conveniently located just 15 minutes from both Chestertown, MD and Middletown, DE, this waterfront retreat offers the ideal blend of comfort, convenience, and outdoor enjoyment. A must-see!

31923 River Park Rd, Millington

Listing courtesy of RE/MAX Chesapeake. 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:

$425,000

Investment Opportunity Commercial and Mult- Family rentals - The current commercial space is being used for an antique store. Great location on corner lot. The parcels are known as 1502004674 and 1502004666, zoned B-1 and V. The V zoning includes two dwellings offering a total of 3 apartments that are currently rented. The buildings offer a lot of character and charm, just waiting for you next business idea.

26622 Medders Rd, Still Pond

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

$315,000

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.

2 Beds ⋅ 2 Baths

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:

$398,000

Warm and Welcoming 3-Bedroom Colonial with a Private Backyard and spacious primary suite. Come home to the comfort and charm of this inviting 3-bedroom, 2.5-bath Colonial, tucked into a peaceful country setting while still offering convenient access to points north. From quiet mornings to busy afternoons and relaxed evenings, this home provides a warm, easy-flowing layout designed for everyday living and time spent together. The spacious primary suite offers a comfortable place to recharge at the end of the day, while two additional bedrooms provide room for family, guests, a nursery, playroom, or home office. With 2.5 baths, the layout makes daily routines easier and helps keep everyone moving smoothly on busy mornings. Step outside to a fenced-in backyard where there is space to play, garden, entertain, or simply enjoy the fresh air in privacy. Blending classic character with a comfortable country feel, this home is a wonderful place to make memories and settle into a lifestyle that feels both peaceful and connected.

Warm and Welcoming 3-Bedroom Colonial with a Private Backyard and spacious primary suite. Come home to the comfort and charm of this inviting 3-bedroom, 2.5-bath Colonial, tucked into a peaceful country setting while still offering convenient access to points north. From quiet mornings to busy afternoons and relaxed evenings, this home provides a warm, easy-flowing layout designed for everyday living and time spent together. The spacious primary suite offers a comfortable place to recharge at the end of the day, while two additional bedrooms provide room for family, guests, a nursery, playroom, or home office. With 2.5 baths, the layout makes daily routines easier and helps keep everyone moving smoothly on busy mornings. Step outside to a fenced-in backyard where there is space to play, garden, entertain, or simply enjoy the fresh air in privacy. Blending classic character with a comfortable country feel, this home is a wonderful place to make memories and settle into a lifestyle that feels both peaceful and connected.

200 School St, Millington

Listing courtesy of Gunther-McClary Real Estate. Contact:

$147,000

Build your dream home in Little Neck Farm! Lot #30 is a spacious residential property on Hagy Road with a deeded deep-water boat slip. The future home site offers beautiful pastoral views and is nicely edged with crape myrtles and evergreens. The deeded boat slip, located in the Little Neck community waterfront, is just a short stroll or drive away. The community docks were recently updated and replaced! The deeded boat slip #4 has lights, electric, and water. The waterfront also features space to store and launch a kayak, picnic tables, and a storage shed. Enjoy the peaceful open space and protected shorelines in Little Neck. Peaceful location, yet only 10 minutes to downtown Rock Hall, which offers two small grocery stores, ample shops, restaurants, and festivals throughout the year! This property is a prime location with water access, perfect for a full-time home or weekend getaway.

Lot 30 Hagy Rd, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$895,000

****NEW PATH TO WATER FOR YOUR GATOR OR UTV**** This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect "magnet house" to attract friends and family or an amazing investment opportunity.

****NEW PATH TO WATER FOR YOUR GATOR OR UTV**** This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect "magnet house" to attract friends and family or an amazing investment opportunity.

24050 Macs Ln, Worton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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!

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:

$1,495,000

106 Acre Recreational Farm Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. Regulations prohibit surrounding farms from growing communities. BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE. Narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments gives hunting sites spread throughout. Recent Selective Forrest management work has improved the hunt ability offering additional trails and food plot areas. Home was moved approx 20 years siting onto a new foundation then renovated to enjoy the views and ready for its new owners. Horses, we have some fencing, turn in shed, 4 stall to the rear of 3 level barn giving you plenty of room for storage of hay, straw and feed. And think how much fun to ride through and impoundment? Almost adjoins the 4,000 Millington Wildlife Preserve, with riding trails. Remember this area is protected from the surrounding farms becoming communities and the end of your dreams. Haven’t you work Hard all these Years? Reward yourself now with unique Opportunity while it’s available. Do not enter property without appointment and listing agent. New County Zoning change This would make a great extra income opportunity Possible Farm Wedding site ** IMAGINE A NEW CLASIC BARN AND MAYBE EVEN A GAZIBO BOTH OVERLOOKING THE LARGEST POND INCLUDING LANDSCAPING, PARKING AND OTHER FEATURES TO THIS UNIQE PROPERTY. LETS TALK ABOUT IT… PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

106 Acre Recreational Farm Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. Regulations prohibit surrounding farms from growing communities. BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE. Narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments gives hunting sites spread throughout. Recent Selective Forrest management work has improved the hunt ability offering additional trails and food plot areas. Home was moved approx 20 years siting onto a new foundation then renovated to enjoy the views and ready for its new owners. Horses, we have some fencing, turn in shed, 4 stall to the rear of 3 level barn giving you plenty of room for storage of hay, straw and feed. And think how much fun to ride through and impoundment? Almost adjoins the 4,000 Millington Wildlife Preserve, with riding trails. Remember this area is protected from the surrounding farms becoming communities and the end of your dreams. Haven’t you work Hard all these Years? Reward yourself now with unique Opportunity while it’s available. Do not enter property without appointment and listing agent. New County Zoning change This would make a great extra income opportunity Possible Farm Wedding site ** IMAGINE A NEW CLASIC BARN AND MAYBE EVEN A GAZIBO BOTH OVERLOOKING THE LARGEST POND INCLUDING LANDSCAPING, PARKING AND OTHER FEATURES TO THIS UNIQE PROPERTY. LETS TALK ABOUT IT… PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

13235 Knotts Ln, Golts

Listing courtesy of Meredith Fine Properties. 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:

$1,495,000

Hidden away at the end of country lane Privacy awaits Surrounded by woods 106 Acres Hunting Farm in North East Kent County. Government regulation's insure surrounding farms will remain rather than growing communities. About 60 acres woods, 26 acres of grain fields, with over 7 acres impoundments, deep ponds for fishing plus a wood duck pond in the woods. Impoundments are equipped with water level control. Buyer to verify acreage 1900 farm home renovated about 20 yrs. Ago including new heat pump. Three Bedrooms, 2 Full Baths, Dining Room, Living Room, Family Room with Fireplace. Enjoy the picturesque views of farm from 2nd floor deck off master bedroom Perfect setting for Canadian geese to spend the nights adding to your enjoyment. Recent Selective Forestry work completed improved opportunity with additional trails and food-lots areas add shelter food for wildlife. Some fencing & 4 stalls behind the barn for horses plus a turn in shed. Many nice duck hunting properties are impacted by global warming rising sea level not an issue here. Elevation is well over 50 feet above sea level, so you a safe investment that can be enjoyed for generations to come. And surrounding farms protected from becoming communities and ending your dreams. Listed on June 20, 2026 some sites say several years which is not accurate. Featuring Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself..20 minutes from Middletown, De that offers sales tax free shopping and dining. Possible extra income farm wedding site subject to county approval. ** IMAGINE A NEW CLASSIC BARN AND PERHAPS A GIZABO OVERLOOKING THE LARGEST POND? ADD IN A GREAT LANDSCAPING PARKING AND FEATURES FOR A DESIRABLE DESTINATION. WITH SO MANY PEOPLES SO CLOSE. Wilmington, Towson & Bay Bridge about 50 minutes. Philadelphia and West Chester about 90 minutes. Almost adjoins the 4,000 Millington Wildlife Preserve. Google it to see what’s available. HERE IS YOUR CHANCE * STEP UP, AND ENJOY A GENERATIONAL TREASURE! Do not enter property without appointment and with Listing Agent. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

Hidden away at the end of country lane Privacy awaits Surrounded by woods 106 Acres Hunting Farm in North East Kent County. Government regulation's insure surrounding farms will remain rather than growing communities. About 60 acres woods, 26 acres of grain fields, with over 7 acres impoundments, deep ponds for fishing plus a wood duck pond in the woods. Impoundments are equipped with water level control. Buyer to verify acreage 1900 farm home renovated about 20 yrs. Ago including new heat pump. Three Bedrooms, 2 Full Baths, Dining Room, Living Room, Family Room with Fireplace. Enjoy the picturesque views of farm from 2nd floor deck off master bedroom Perfect setting for Canadian geese to spend the nights adding to your enjoyment. Recent Selective Forestry work completed improved opportunity with additional trails and food-lots areas add shelter food for wildlife. Some fencing & 4 stalls behind the barn for horses plus a turn in shed. Many nice duck hunting properties are impacted by global warming rising sea level not an issue here. Elevation is well over 50 feet above sea level, so you a safe investment that can be enjoyed for generations to come. And surrounding farms protected from becoming communities and ending your dreams. Listed on June 20, 2026 some sites say several years which is not accurate. Featuring Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself..20 minutes from Middletown, De that offers sales tax free shopping and dining. Possible extra income farm wedding site subject to county approval. ** IMAGINE A NEW CLASSIC BARN AND PERHAPS A GIZABO OVERLOOKING THE LARGEST POND? ADD IN A GREAT LANDSCAPING PARKING AND FEATURES FOR A DESIRABLE DESTINATION. WITH SO MANY PEOPLES SO CLOSE. Wilmington, Towson & Bay Bridge about 50 minutes. Philadelphia and West Chester about 90 minutes. Almost adjoins the 4,000 Millington Wildlife Preserve. Google it to see what’s available. HERE IS YOUR CHANCE * STEP UP, AND ENJOY A GENERATIONAL TREASURE! Do not enter property without appointment and with Listing Agent. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

13235 Knotts, Golts

Listing courtesy of Meredith Fine Properties. 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!