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6445 Edesville Rd, Rock Hall
$258,000
4 Beds ⋅ 2 Baths
Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields.

6445 Edesville Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Doug Ashley Realtors, LLC.

318 Lincoln, Chestertown
$255,000
3 Beds ⋅ 2 Baths
Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

318 Lincoln, Chestertown

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

Selling Office: Samson Properties of DE, LLC.

112 Metcalf Rd, Chestertown
$250,000
3 Beds ⋅ 2 Baths
This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed—perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.

112 Metcalf Rd, Chestertown

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

112 Elm St, Chestertown
$249,000
3 Beds ⋅ 1 Baths
Sought after location in College Heights. Short walk to downtown Chestertown and Parks. This cozy rancher is a diamond in the rough and is ready for new owners! located on a safe and quiet street, with public water and sewer with municipal pickups. Don't miss your opportunity to live in a great location! Being sold as is and priced accordingly.

112 Elm St, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Bayside Realty.

107 Conley Dr, Chestertown
$245,000
3 Beds ⋅ 1 Baths
Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

107 Conley Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Cummings & Co. Realtors.

21217 Texas Ave, Chestertown
$244,000
2 Beds ⋅ 1 Baths
MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

21217 Texas Ave, Chestertown

Listing courtesy of RE/MAX Leading Edge. Contact:

Selling Office: Cross Street Realtors LLC.

100 Metcalf Rd, Chestertown
$240,000
3 Beds ⋅ 2 Baths
🏡 💎 Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K 🎉 Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! ✨ Your Dream Home Checklist: ✅ * NO HOA! Freedom & Savings! 💸 * One-Level Living: Easy breezy! 🚶‍♀️ * Open Concept: Perfect for entertaining! 🛋️ The heart of the home is the spectacular eat-in kitchen! You'll love the white shaker cabinets, dazzling granite countertops, and sleek stainless steel appliances. 🍳 The main areas feature gorgeous LVP flooring, while cozy carpet warms the bedrooms. Step outside to your private covered patio for morning coffee ☕ or evening relaxation. 🌞 With a generous 5,914 sq ft lot, there's plenty of room for fun! 🌳 Retreat to your private primary suite 👑 with a spa-like en-suite and walk-in shower. 🚿 Embrace the Chestertown Life! ⚓ This prime spot is minutes from historic downtown charm! Enjoy the weekly farmers market 🥕, shops, galleries 🖼️, and waterfront festivals like the famous Downrigging Weekend ⛵. This golden opportunity won't last long! Be the first to call this exquisite property "home." 🔑 Your new beginning starts here! ❤️

100 Metcalf Rd, Chestertown

Listing courtesy of Bayside Realty. Contact:

Selling Office: Douglas Realty LLC.

381 Hurtt Ave, Millington
$237,500
2 Beds ⋅ 1 Baths
Charming and affordable 2-bedroom, 1-bath bungalow tucked away on a quiet street. This move-in ready home has been well maintained and features a newer metal roof for long-term durability and peace of mind. Ideal as a starter home or for anyone looking to downsize without sacrificing space. Enjoy a large lot plus a detached two-car garage complete with electricity and propane heat — perfect for hobbies, storage, or a workshop. Conveniently located just minutes from Route 301 for an easy commute while still offering a peaceful setting.

381 Hurtt Ave, Millington

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

21263 Allens Ln, Rock Hall
$235,000
3 Beds ⋅ 2 Baths
Older house that sets on 4.58 acres of land. Very quiet with views of the open acreage behind the house. A few sheds on the property and located near the end of the street. Walking distance to the public water.

21263 Allens Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

7521 Pine Ave, Chestertown
$235,000
3 Beds ⋅ 1 Baths
Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and central heat/air. Competitively priced and full of potential!

7521 Pine Ave, Chestertown

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

Selling Office: Doug Ashley Realtors, LLC.

26109 Lambs Meadow Rd, Worton
$235,000
4 Beds ⋅ 3 Baths
Spacious and versatile, this 4-bedroom, 2.5-bath home offers endless possibilities! Perfectly situated on a large corner lot and zoned Village, the property features a first-floor bedroom with a private entrance—ideal for a home office, daycare, or other business use. When purchased in 2020 it received a new roof, septic, and well, and more recently the seller has updated the 2nd-floor HVAC system for added efficiency and comfort. Inside, you’ll love the large eat-in kitchen, brick sunroom filled with natural light, and dual-zone heating & air. Located just minutes from downtown Chestertown and some of the area’s most popular marinas, this property combines small-town convenience with Chesapeake lifestyle charm & business potential!

26109 Lambs Meadow Rd, Worton

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

Selling Office: TTR Sotheby's International Realty.

126 Metcalf Rd, Chestertown
$230,000
3 Beds ⋅ 2 Baths
Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside the primary bedroom. This property is at the end of Metcalf Rd.

126 Metcalf Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Benson & Mangold, LLC..

11029 Brindley Dr, Worton
$229,000
2 Beds ⋅ 1 Baths
Welcome to 11029 Brindley Drive that is move-in ready with new flooring, heat/air and has been freshly painted. The open floor plan offers great family time and the back yard backs to trees which now offers privacy and shade for picnics and play. Convenient to Parks and Recreation with a public beach only minutes away.

11029 Brindley Dr, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Maryland Heritage Properties.

202 Pine St, Chestertown
$222,000
3 Beds ⋅ 1 Baths
Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights.A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

202 Pine St, Chestertown

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

Selling Office: Taylor Properties.

5548 Boundary Ave, Rock Hall
$220,500
2 Beds ⋅ 1 Baths
Adorable small 2 Bedroom, 1 Bath, home located in the eventful town of Rock Hall. A great starter home or 2nd home while you're visiting Rock Hall on your boat. An affordable, easily maintained home within walking or biking distance to restaurants, shopping and marinas. Cute front porch to sit and enjoy your days and evenings.

5548 Boundary Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Advantage Realty.

100 Prospect St, Chestertown
$215,000
3 Beds ⋅ 1 Baths
Fully Renovated Rancher in the Heart of Chestertown — Walk to Everything. Most homes in this price range make you choose: updated systems or a great location. This one delivers both. Tucked on a quiet corner lot just steps from Washington College, the Chester River marina, weekend Farmers Market, and Chestertown's thriving restaurant and shop scene, 100 Prospect Ave puts the best of the Eastern Shore's most walkable town right outside your front door — without the noise or traffic. The home has been completely overhauled from the outside in. New metal roof, gutters, downspouts, vinyl siding, and windows protect your investment from the elements before you ever step inside. Inside, a new HVAC system, updated 200-amp electrical panel, new hot water heater, and fully replaced water main and plumbing mean zero deferred maintenance — just move in and live. Refinished hardwood floors and new vinyl flooring run throughout open, light-filled spaces. The updated bathroom features a new vanity, and the laundry room comes equipped with a brand-new washer and dryer. The kitchen opens directly into the dining area and flows into the family room — a layout that makes everyday living easy and entertaining effortless. Start your mornings on the enclosed porch. Host friends on a generous corner lot with room to breathe. Park conveniently on the private gravel pad with direct kitchen access. This is what move-in ready actually looks like. Schedule your tour today.

100 Prospect St, Chestertown

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

Selling Office: Bayside Realty.

31858 River Park Rd, Millington
$207,000
2 Beds ⋅ 1 Baths
Don’t miss this opportunity to own your own home for rental prices! Come see this updated, functional, and move-in ready home with some very major improvements already done! This charmer offers easy, one level living. Big-ticket updates completed in 2025, including a new roof and new windows (most not all replaced), giving buyers peace of mind from day one. The standout feature is the renovated bathroom with a premium walk-in soaking tub (approx. $10K upgrade) which is ideal for comfort, accessibility, and long-term convenience. The layout offers flexibility with multiple bedroom options, including a pass-through room perfect for an office, nursery, or cozy sitting space. Park in the attached garage or use it as a combo craft room/storage/workshop.....lady/man cave! High ceilings and shelving, as well as both exterior and interior access doors make this a fabulous bonus space. Enter the house from the garage to a mudroom/pantry, just off of the kitchen! Outside, enjoy a flat, usable yard and ample driveway parking. ** Homes with this combination of updates, usability, and VALUE are hard to find — call to schedule your showing early!

31858 River Park Rd, Millington

Listing courtesy of Taylor Properties. Contact:

Selling Office: Village Real Estate Company LLC.

21363 Lynn Ln, Chestertown
$205,000
3 Beds ⋅ 1 Baths
Take advantage of the Eastern Shore's amenities and quality of life in this low maintenance one floor home just a hop and a skip from the Chesapeake Bay and public beach. The Sergeant's Quarters at Tolchester Village is located less than 15 minutes from both Chestertown and Rock Hall providing nearby cultural, entertainment, and employment opportunities. The home itself has been taken care of with love and is ready for its next steward. Vaulted ceilings and spacious room sizes provide a great feel. The Shanty Bar at Tolchester Marina, just a beach cruiser or golf cart ride away, is one of the Chesapeake Bay's premier beachfront establishments serving coastal fare, fresh made boat drinks, and hosting live music on the Bay. Invest wisely in this tranquil retreat with bountiful nearby attractions.

21363 Lynn Ln, Chestertown

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

Selling Office: Doug Ashley Realtors, LLC.

206 Virginia Ave, Galena
$205,000
3 Beds ⋅ 2 Baths
Are you looking for a classic home with a ton of charm? Do you love original wood floors? Not afraid of updating? This could just be the home for you! Screened in porch welcomes you to a beautiful foyer, and a classic living room with a fireplace that has been closed up but still provides a nice focal point. Owner is not sure if it could become a working wood-burning fireplace or not, but a gas fireplace may be possible. There is an office area off of the dining room, kitchen has been updated and a full bath and laundry room for your convenience on the first floor. Upstairs there are three bedrooms and one bathroom. There is a storage shed that has seen better days, and a newish three car garage with a workshop in one of the bays. Two doors open automatically with the shop area door being opened the old-fashioned way. This is a fun house with so much potential. The current owner has put a new roof on the home in July of this year & a new water line to the home in 2023. Public water and sewer and trash pickup is included in the quarterly payment of $276.50 +/-. Easy to show! Cash or Conventional Financing only.

206 Virginia Ave, Galena

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

139 Prospect St, Chestertown
$195,000
3 Beds ⋅ 1 Baths
Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in kitchen—perfect for everyday living and easy entertaining. A private hallway leads to a generously sized primary bedroom and two additional spacious bedrooms. Outside, enjoy off-street parking and a large, deep backyard ideal for relaxing, gardening, or gathering. Conveniently located just moments from downtown Chestertown’s shops, restaurants, and local attractions, this property is a wonderful opportunity as a full-time residence, weekend retreat, or investment property. An exceptional value just minutes from the charm and amenities of historic downtown Chestertown! Mortgage savings may be available for buyers of this listing.

139 Prospect St, Chestertown

Listing courtesy of Redfin Corp. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

423 Calvert St, Chestertown
$190,000
3 Beds ⋅ 2 Baths
Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely updated with all new fixtures and finishes. The main level offers ample living space, dinging room and new kitchen and laundry. Upstairs you will find three bedrooms and a full bathroom, with access from the primary bedroom as well. Outside, enjoy a newly fenced backyard, updated shed, and an extra-deep lot offering the potential for additional rear parking. A new roof installed in 2024 adds even more value and peace of mind. Boasting generous space and extensive upgrades throughout, this home presents an exceptional opportunity for a primary residence, weekend getaway, or investment property. Ideally located just moments from downtown shopping, dining, and the waterfront, you’ll love the walkable lifestyle and charm that Chestertown has to offer.

423 Calvert St, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

327 Cypress St, Millington
$190,000
4 Beds ⋅ 1 Baths
This cottage-style home currently offers four bedrooms and one full bath, with the flexibility to reconfigure room usage to suit your vision. The nicely sized kitchen is open to the living room, creating a central gathering space with renovation potential. A rear entrance leads into a small mudroom, adding everyday convenience, while the basement—accessible from either interior like it orginally was or current exterior entrance—provides additional storage, workshop, or future-use possibilities. The home has been well-lived in over the years and is now ready to be brought back to life. Set on a long, deep lot, the property offers ample outdoor space for gardens, an outbuilding for projects, or a peaceful path leading down toward the water’s edge. Additional features include town water and town sewer. Conveniently located just off Route 301, this as-is property allows for an easy commute north towards Middletown or south towards Bay Bridge, with Dover approximately 30 minutes away. Ideal for investors, renovators, or buyers looking for a project to make their own.

327 Cypress St, Millington

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

Lot 9 Prestwick, Chestertown
$185,000
Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area s finest builders.

Lot 9 Prestwick, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

31695 Olivet Cir, Galena
$182,000
3 Beds ⋅ 2 Baths
Welcome Home to 31695 Olivet Circle, this 3 bedroom 2 bath home is a great started home! Beautiful property with lots of possibilities! Off the beaten path & surrounded by nature with a detached garage.

31695 Olivet Cir, Galena

Listing courtesy of RE/MAX Chesapeake. Contact:

Selling Office: Unrepresented.

9925 Flatland Rd, Chestertown
$180,000
3 Beds ⋅ 2 Baths
As - Is

9925 Flatland Rd, Chestertown

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Non Subscribing Office.

23069 Raleigh Rd, Chestertown
$175,000
2 Beds
Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Renters finally moved out and the house is being cleaned up. Roof was replaced in 2022.

23069 Raleigh Rd, Chestertown

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

Selling Office: Doug Ashley Realtors, LLC.

22783 Mckinleyville Rd, Rock Hall
$170,000
3 Beds ⋅ 3 Baths
Classic farm house on half an acre, just a stones throw from the Rock Hall Yacht Club and Langford Bay Marina. The main home has two full bathrooms and two bedrooms. The large screened-in porch overlooks the spacious yard. A nice spot to catch a breeze from the water. Additionally there is guesthouse with a full bath and kitchen. There are two small storage sheds on the property. The houses have solid bones, but are in need of a full remodel. Amazing location and tons of potential!

22783 Mckinleyville Rd, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: VYBE Realty.

144 Prospect St, Chestertown
$165,000
2 Beds ⋅ 2 Baths
Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county

144 Prospect St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Execuhome Realty.

6179 E Dorlon Dr, Rock Hall
$165,000
3 Beds ⋅ 1 Baths
OFFERS DUE BY MONDAY, 12/22 AT 6PM. Don't miss this sweat-equity opportunity! Welcome to 6179 E Dorlon Drive in Rock Hall, MD—a 3-bedroom, 1-bath home full of potential for the right buyer! This property is ideal for investors, renovators, or buyers looking to build equity through updates and improvements. With some TLC, this home offers the chance to customize, renovate, or reposition as a rental or resale investment. Conveniently located just 10 minutes from Chestertown, you’ll enjoy easy access to shopping, dining, Washington College, and local amenities, while still being close to the charm and waterfront lifestyle Rock Hall is known for! Whether you’re looking for your next fix-and-flip, long-term rental, or a home you can make your own over time, this property presents a solid opportunity in a desirable area. Bring your vision and unlock the potential as this home is priced to sell! Property is being sold as-is.

6179 E Dorlon Dr, Rock Hall

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

Selling Office: RE/MAX Executive.

21316 Persimmon Dr, Chestertown
$160,000
2 Beds ⋅ 1 Baths
Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all electric with a washer/dryer located on the main level. Affordable, and the opportunity to express your own vibe and decorating skills. Call for more information.

21316 Persimmon Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Samson Properties.

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