Refine Search
Map
Sort by
101 S Mill St, Chestertown
$500,000
2 Beds ⋅ 3 Baths
This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

101 S Mill St, Chestertown

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

Selling Office: Long & Foster Real Estate, Inc..

515 N Kent St, Chestertown
$495,000
4 Beds ⋅ 3 Baths
Nestled in the charming Byford Development, this beautifully renovated home exudes warmth and comfort, making it the perfect retreat. With a thoughtful renovation completed in 2020, this residence boasts a blend of traditional and farmhouse styles, featuring a stunning brick and vinyl exterior that invites you in. Step inside to discover a spacious 2,220 sq. ft. layout, where modern amenities meet classic charm. The heart of the home is the gourmet kitchen, complete with upgraded countertops, stainless steel appliances, and a convenient island that encourages gatherings. This home offers four generous bedrooms and 2.5 bathrooms. Enjoy the comfort of hardwood floors throughout the main level, complemented by ceiling fans and window treatments that enhance the cozy atmosphere. The main floor laundry adds convenience to your daily routine, while the unfinished basement provides ample storage or potential for future expansion. Outside, the circular driveway and attached garage offer easy access and plenty of parking. Set on a spacious 0.34-acre lot, this home is a perfect blend of comfort and functionality, ready to welcome you home. Don't miss the opportunity to make this inviting space your own!

515 N Kent St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Benson & Mangold, LLC.

201 Greenwood Ave, Chestertown
$495,000
4 Beds ⋅ 3 Baths
An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with fireplace, first floor primary bedroom with cathedral ceiling, Florida room, full basement with fireplace and a 2 car attached garage. The primary bath and Florida room both have radiant floor heating. The 3 bedrooms on the second level are spacious and offer built-ins. There is even a family room with built-ins! The kitchen has all of the major appliances and granite counters. This home has wood floors throughout most of the house. Oil heat, heat pump and central A/C provide for indoor comfort year round. A rear deck provides for outdoor enjoyment. There is a shed for additional storage. This home is situated on a corner and just a short distance to shopping, hospital and downtown Historic Chestertown.

201 Greenwood Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

218 Camelot Dr, Chestertown
$495,000
5 Beds ⋅ 4 Baths
Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor living zones perfect for entertaining, with direct access from the breakfast room. Inside, a light filled two story foyer welcomes you with elegant architectural details including crown molding, chair rail, wainscoting, turned stair railings, and hardwood floors throughout the main level. Neutral paint enhances the home’s timeless appeal. The gourmet kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances (including a French door refrigerator), custom cabinetry, pantry, granite countertops, tile backsplash, and a center island with breakfast bar. The adjoining breakfast room or bonus space, framed by picture windows and a cathedral ceiling, is perfect for morning coffee or hosting holiday celebrations. The main level offers formal living and dining rooms, a convenient powder room, and a spacious family room highlighted by a floor to ceiling stone, wood burning fireplace with raised hearth and custom stone mantel—an inviting gathering space for family and friends. Upstairs, the primary suite is thoughtfully positioned for privacy and boasts double door entry, a walk-in closet plus an additional closet, and a luxurious ensuite bath with dual vanity, soaking tub, and stall shower. Three additional generously sized bedrooms and a full hall bath complete the upper level. The finished walk out lower level expands your living space with a large recreation area, a possible fifth bedroom, full bath with stall shower, a finished bonus room ideal for a fitness area or media room, and an oversized laundry, utility, and storage area with abundant space for seasonal and long-term storage. Conveniently located just minutes from shopping and local dining favorites, and a short drive to Historic Chestertown along the Chester River, you’ll enjoy easy access to charming boutiques, restaurants, galleries, Washington College, and rich cultural and historical attractions.

218 Camelot Dr, Chestertown

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Samson Properties.

14525 John Peel Rd, Golts
$490,000
3 Beds ⋅ 3 Baths
Welcome to 14525 John Peel Road, a beautifully maintained home offering the perfect blend of elegance, comfort, and scenic surroundings in a highly desirable location. Set on a generous one and a half-acre lot, this 3-bedroom, 2.5-bathroom residence provides both privacy and a strong sense of community, complete with access to a community pier—ideal for enjoying the surrounding views and waterfront lifestyle. Inside, the home has been refreshed with new carpet and fresh paint, creating a clean, inviting atmosphere throughout. The eat-in kitchen offers a warm and functional space for everyday meals, with easy access to a charming, covered porch—perfect for sipping morning coffee or dining al fresco. The spacious family room with a pellet burning fireplace serves as a welcoming centerpiece for relaxing evenings or gatherings with friends and family. Step outside to your own backyard retreat, featuring a beautiful above-ground pool with an expansive deck, perfectly designed for entertaining and summer enjoyment. Whether hosting guests or unwinding while taking in the peaceful views, this outdoor space truly enhances the home’s appeal. With its exceptional location, tasteful updates, and a seamless mix of indoor comfort and outdoor enjoyment, this property offers a lifestyle that is both refined and relaxed. A wonderful opportunity to own a home that combines charm, functionality, and beautiful surroundings. Propane tank is owned!!!

14525 John Peel Rd, Golts

Listing courtesy of Corner House Realty. Contact:

Selling Office: Sky Realty.

31569 Jim Davis, Galena
$490,000
5 Beds ⋅ 3 Baths
Welcome to this spacious 5-bedroom, 2.5 bath raised ranch located on picturesque Jim Davis Road in Galena, MD, offering peaceful country living on 2 acres with convenient access to surrounding areas. Enjoy a circular driveway and detached garage providing plenty of room for parking, hobbies, and guests. Step outside to your own private retreat featuring an inground pool, pool shed, deck, patio, and privacy fencing - perfect for summer entertaining and relaxation. The property also offers a play area and beautiful views of local farms, creating a serene and scenic setting. Inside, the home offers a flexible layout with extra living space in the finished basement, while all bedrooms are located above ground on the first floor. PREFER the opposite setup? The layout can easily be adjusted to fit your needs-whether you want more entertaining space, guest rooms, or a home office. For added peace of mind, the seller is providing a ONE YEAR HOME WARRANTY**** through American Home Shield. Galena is such an adorable little town with tons of charm & character. Now priced to SELL Conveniently located close to Delaware, Baltimore, and Pennsylvania, this home blends rural charm with commuter-friendly access. A unique opportunity offering space, privacy, and versaltility-schedule your private showing today!

31569 Jim Davis, Galena

Listing courtesy of Remax Vision. Contact:

Selling Office: RE/MAX Associates-Hockessin.

100 Adela Way, Chestertown
$490,000
4 Beds ⋅ 4 Baths
*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptional versatility, featuring its own private entrance, kitchenette, full bath with steam sauna, and open-concept living/bedroom area—perfect for guests, or entertaining. A dedicated workroom completes the lower level, ready for projects or hobbies. Outside, enjoy your fenced-in backyard oasis complete with a deck. This home has been meticulously cared for and thoughtfully updated, including: New roof, gutters, and gutter covers (2025) New HVAC system – furnace and A/C (2024) New 80-gallon water heater (2022) Fully renewed basement (2022) with new flooring, carpet, paint, and dual sump pumps Finished garage (2022) Ornamental Fence (2020) Furnishings Negotiable .

100 Adela Way, Chestertown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Keller Williams Gateway LLC.

25428 Worton Lynch Rd, Worton
$475,000
3 Beds ⋅ 3 Baths
Welcome to 25428 Worton Lynch Road in Worton, Maryland! Situated on 1.28 acres, this charming 3-bedroom, 2.5-bath home offers comfortable living with thoughtful features throughout. The heart of the home is the kitchen, featuring granite countertops, LVP flooring, and ample cabinet space for cooking and entertaining. Just off the kitchen, the inviting living room boasts beautiful hardwood floors, a shiplap accent wall, and an electric fireplace that creates a warm and welcoming atmosphere. A convenient half bath is also located on the first floor for guests. The spacious first-floor primary suite provides a private retreat with a large walk-in closet, a hidden closet for additional storage, and an ensuite bathroom complete with a tiled shower. Upstairs, you'll find two additional bedrooms with carpeting and a full bathroom, offering comfortable space for family or guests. A full basement with a wood stove adds valuable storage, workshop potential, or future finishing possibilities. Outside, enjoy the peaceful setting from the rear deck overlooking the 1.28-acre property. Additional features include a shed with a concrete pad and a swing set that conveys with the sale. Offering the perfect blend of comfort, space, and country charm, this Worton property is ready to welcome its next owners home.

25428 Worton Lynch Rd, Worton

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

Selling Office: Century 21 Gold Key Realty.

101 Birch Run Rd, Chestertown
$475,000
3 Beds ⋅ 2 Baths
Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 Acres Discover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout. Step inside to find a bright, open-concept layout where the brand-new kitchen flows seamlessly into the family room—perfect for entertaining or relaxing by the cozy fireplace. The kitchen features sleek finishes, contemporary cabinetry, stylish lighting, and premium appliances. Both full baths have been fully renovated with today’s top design trends, creating a spa-like experience at home. The home’s thoughtful floor plan and attention to detail shine through every room—from fresh flooring and fixtures to elegant accents that elevate the overall aesthetic. Enjoy peace of mind with a new roof featuring 50-year architectural shingles (transferable warranty included). The oversized two-car garage provides ample space for parking and storage, while the landscaped .42-acre lot offers just the right amount of yard to enjoy without a lot of upkeep. Ideally situated within walking distance to the Chester River, Washington College, and Chestertown’s charming downtown —boutiques, shops, restaurants, and regular community events await. Bring your boat, kayak, paddle-board, or jet ski and experience the best of Eastern Shore living!

101 Birch Run Rd, Chestertown

Listing courtesy of Remax Vision. Contact:

Selling Office: RE/MAX Real Estate Connections.

31729 W Edge Rd, Millington
$470,000
3 Beds ⋅ 3 Baths
Spacious waterfront rancher with pole barn—priced below appraised value for a quick sale! Appraised at $534K, this motivated seller is offering a rare opportunity for instant equity on the upper Chester River. Conveniently located with easy access to Rt. 301, making commuting to Philadelphia, Middletown, or the Chesapeake Bay Bridge surprisingly convenient while still enjoying the perks of waterfront living. This well-maintained 3-bedroom, 2.5-bath rancher offers comfortable one-level living with beautiful river views throughout. The inviting living room features a stone propane fireplace, while the spacious primary suite includes a second gas fireplace, oversized bath with garden tub, walk-in shower, and private water closet. The kitchen was designed with both entertaining and everyday living in mind, featuring an island, double ovens, farmhouse sink, and river views right from the window. The dining area opens to a rear deck with retractable awning—perfect for relaxing evenings overlooking the water. One of the standout features is the impressive 1,200 sq. ft. pole barn connected by a breezeway. Complete with a second level and motorized lift, this space is ideal for contractors, hobbyists, boat storage, workshop space, car enthusiasts, or anyone needing serious storage and flexibility. Outside, enjoy kayaking and fishing right from your own property. The home is elevated well above the floodplain and may offer future options for water access improvements such as steps, a bulkhead, or small pier (buyer to confirm with county). Additional highlights include public water and sewer, a separate irrigation well, professionally landscaped grounds, regularly serviced HVAC, resealed driveways, and proactive maintenance throughout. Less than a mile to Food Lion and convenient to Chestertown, Middletown, and Bay Bridge travel routes. Freshened up for spring and ready for its next owner—add this waterfront opportunity to your watch list before it’s gone! All offers considered.

31729 W Edge Rd, Millington

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

Selling Office: Keller Williams Legacy.

311 Devon Dr, Chestertown
$465,000
4 Beds ⋅ 3 Baths
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom suite on each level; and with there being three additional bedrooms, makes a total of five bedrooms or extra rooms for whatever the need may be. The home offers a garage as well as a full unfinished walk-out basement. The pictures prove the true beauty and spaciousness of this home. (room dimensions are approximate)

311 Devon Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

121 1st Ave, Betterton
$461,000
4 Beds ⋅ 2 Baths
Multiple offers received- Highest and Best due by 6/17 at noon! This property truly has a little something for everyone! Spacious 4-bedroom, 2-bath rancher situated on 1.94 private acres in the charming waterfront town of Betterton. Featuring a full walkout basement, attached 2-car garage, and a 30x40' pole building, there’s plenty of room for hobbies, storage, boats, workshops, or recreational toys. Step onto the welcoming screened front porch and into the cozy living room with a wood-burning fireplace. The recently remodeled kitchen features quartz countertops, new matte stainless appliances, double ovens, and plenty of space for cooking and gathering. The dining room, complete with a pellet stove, opens to the 12x20' composite back deck overlooking the peaceful wooded setting. The spacious primary suite offers a walk-in closet and private full bath. Two additional bedrooms and an updated full bath complete the main level. Downstairs, the walkout basement adds even more flexibility with a finished bedroom, rough-in for an additional bathroom, and a large open area ready for storage, recreation space, and possibilities. Oversized double doors provide easy access to the backyard. Home features a new roof and heat pump replaced within the past two years! Enjoy privacy surrounded by trees while still being within walking distance to Betterton Beach and the public boat ramp. Known as the “Jewel of the Chesapeake,” Betterton is home to one of the Chesapeake Bay’s best sandy beaches with calm waters, a pavilion, and a laid-back waterfront lifestyle. Conveniently located approximately 20 minutes to Chestertown, 30 minutes to Middletown, 1.5 hours to Philadelphia, and about 1 hour to the Bay Bridge. Add this one to your showing list today! Pics will be posted 6/20

121 1st Ave, Betterton

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

Selling Office: Integrity Real Estate.

105 N Water St Unit 2, Chestertown
$460,000
2 Beds ⋅ 2 Baths
Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence combines historic charm, modern comfort, and an enviable waterfront location. Filled with character and warmth, the home features beautiful hardwood floors, soaring ceilings, tall windows, built-ins, and a wonderful period gas fireplace that creates a welcoming focal point in the spacious living room. Two generously sized bedrooms and two beautifully appointed tiled bathrooms provide comfort and style, while an in-unit washer and dryer add everyday convenience. Generous room sizes and abundant natural light enhance the home's inviting atmosphere throughout. The heart of the home is the expansive kitchen and great room at the rear of the residence, overlooking the river. Designed for gathering, entertaining, and everyday living, this impressive space features gorgeous cabinetry, stainless steel appliances, gas cooking, abundant counter space, a farmhouse sink, sunny windows, and plenty of room for dining as well as additional living space. Whether hosting friends, enjoying a quiet morning coffee, or unwinding at the end of the day, it's a room you'll find yourself gravitating toward again and again. Just off the great room, the private balcony overlooks the Chester River and offers sweeping water views in a peaceful waterfront setting. Direct water access and a dedicated boat slip make it easy to enjoy the area's iconic Chester River and everything that life on the water has to offer. Chestertown is steeped in maritime tradition and widely admired for its extraordinary collection of Federal, Georgian, and Victorian architecture. One of the Eastern Shore's most desirable destinations, residents enjoy boutique shopping, fine dining, waterfront attractions, cultural events, and a thriving arts scene. Perfectly positioned along the Chester River, this residence is a historic treasure, a waterfront retreat, and an opportunity to experience the very best of life in one of the Eastern Shore's most cherished communities.

105 N Water St Unit 2, Chestertown

Listing courtesy of Northrop Realty. Contact:

Selling Office: Cross Street Realtors LLC.

206 Camelot Dr, Chestertown
$455,000
4 Beds ⋅ 4 Baths
Enjoy three bedrooms on the main floor, including a spacious primary suite with its own private bath. The open-concept main living area seamlessly connects the kitchen, family room, and bright breakfast/sunroom — making everyday living and entertaining effortless. Hosting something more formal? A separate dining room is ready for the occasion. The second level features a generous living/rec room, plus an additional bedroom and full bath — ideal for guests or even a second primary suite. You choose how it works best for you! The basement offers finished office space and a full bath, along with abundant storage and endless possibilities to create even more living space. Two-car garage - Paved driveway-Brand-new back deck overlooking a fenced backyard- Located directly across from the community space

206 Camelot Dr, Chestertown

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

Selling Office: Samson Properties.

25750 Collins Ave, Chestertown
$450,000
3 Beds ⋅ 2 Baths
Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile. A 40’ x 26’ block 2-car Garage with New insulated doors & openers, built-in shelving, jalousie windows, storage loft and 50% garage extension for Workshop as potential hobby space, home-based business or sporting gear cave. The Garage faces a private parking pad behind the home and a U-shaped driveway to a drive-through carport has the rear door entering a large Foyer convenient for bring in the groceries to the custom built Kitchen with a work-triangle layout. Finishing touches to the renovations are nearly complete, just choose the bedroom Carpeting and move into your New Home! Living Room: Walk along the slate flagstone path and pass through the New, classic Front Door into a spacious Living room featuring an elegant Fireplace and Hardwood floors that extend through a wide open Archway into the Dining room which opens to a comfortable screened Porch—the perfect spot to relax and enjoy the Garden view in this Prestigious neighborhood. Bedrooms: The main floor has a secluded Bedroom Wing with Hardwood floors and full Bathroom with 2 linen closets. A second Bathroom is conveniently close to Foyer and stairwell to Basement: The full Basement features an open Family room with brand-new windows that allow plenty of natural light inside. A side room equipped with a new sump pump well is a perfect blank canvas offering for an Office, Storage or a Rec room. Mechanical & Utillity Room: Separate Electric water heater from Oil boiler to provide comfortable hot water baseboard heat which is supplemented by a new HVAC system for Efficient heating and cooling. Enjoy Resort-like living in this Brick Ranch house only a chip shot away from the Chester River Yacht and Country Club with scenic river views while taking your neighborhood walks, And 5 minute drives along the Chester River, coming and going from your New Home to Historic Chestertown shopping and dining district, also well known for Live Arts, Festivals and home to Washington College.

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

5746 N Main St, Rock Hall
$450,000
The famous Durding's Building in Rock Hall is a landmark property with four rental units. This property was originally an apothecary with a popular soda fountain that continued in operation until just a few years ago. Many of the original fixtures (including the wooden phone booth) are still there. Consisting of two connected buildings on two separate parcels, the offering includes 5742 + 5746 Main Street. 5742 Main has 2,880 sq.ft. with retail space A on the first level and a three bedroom, one bath apartment on the second level. 5746 Main Street has 2,688 sq.ft. with retail space B on the first level and a one bedroom studio apartment above it. Retail space B and the two apartments are under leases. Ready for new owners to purchase and complete a renovation, this historic structure offers an investment in Rock Hall's past and future.

5746 N Main St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: TTR Sotheby's International Realty.

1 Idlewhile Ave Unit 4, Betterton
$449,000
3 Beds ⋅ 3 Baths
Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. Located on a 5 acre setting of beautiful landscape offering carefree living. It includes a community dock and a great private sandy beach. The unit has had upgrades with wood plank tile floors, kitchen with granite countertops, and stainless steel appliances. Living room with gas fireplace has access to screen porch and deck. Large primary bedroom with a balcony. Primary bath has beautiful tiled walk-in shower, new cabinetry and granite countertop. Third floor bedroom offers expansive views of the upper Bay. Full basement with workbench and closet offers plenty of room for all your toys. A new HVAC system was installed 5yrs ago. An 11,000 lb., remote controlled boat lift with E-drive motors is included. Enjoy maintenance free living.

1 Idlewhile Ave Unit 4, Betterton

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

104 Church Aly, Chestertown
$445,000
2 Beds ⋅ 2 Baths
A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

104 Church Aly, Chestertown

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

Selling Office: Unrepresented.

5761 S Main St, Rock Hall
$440,000
The current owner did a lot line adjustment and is selling 5761 Main Street on 3,547 sq.ft. of land. The 1st floor of the building is used for retail space and the 2nd floor is a 2BR/1 bath apartment.

5761 S Main St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

25800 Collins Ave, Chestertown
$435,000
3 Beds ⋅ 2 Baths
Price improvement! Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a few minutes to historic downtown Chestertown.

25800 Collins Ave, Chestertown

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

Selling Office: Northrop Realty.

1 Bayview Rd, Betterton
$435,000
3 Beds ⋅ 2 Baths
Back on the market at no fault of seller. Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom unit is being sold fully furnished and with a deep water boat slip, boat lift and jet-ski lift. As one of the larger units; it has plenty of room for the whole family. Natural light abounds with water views from both balconies or anywhere inside. Galley kitchen with granite countertops and stainless steel appliances. The main floor has an open floor plan, two bedrooms and a full bathroom. Large primary bedroom with ensuite bath and office space upstairs. Plenty of closet space throughout. Full basement has plenty of room for storing outdoor toys and equipment. Recent upgrades include: primary bathroom remodel, waterproof luxury vinyl plank flooring (original hardwoods underneath), carpets, Anderson windows, washer/dryer, water heater, interior doors, paint, and much more. Condo Association just finished renovating the decks and siding. Condo amenities include: private pier with water and electric, designated boat slip with 6,000 pound lift, community pool and kayak storage. Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

1 Bayview Rd, Betterton

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

Selling Office: Village Real Estate Company LLC.

222 Mount Vernon Ave, Chestertown
$433,000
4 Beds ⋅ 2 Baths
This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an adorable kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, you’ll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom and bonus room - perfect for a playroom, office, or workout room. The mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an extra fenced garden area. The driveway has off-street parking for two vehicles. Additional home updates include a tankless hot water heater, high-efficiency 3-zone boiler, whole-house surge protector, upgraded panel, and Kenmore gas range. In summer 2025, the current owners invested in over $60,000 in major renovations hoping to stay for many years. They replaced the roof, updated the electrical wiring, and painted the interior. All upgrades were intended to be enjoyed by current homeowners. Unfortunately, they found that they had to move out of state to be closer to a new job.

222 Mount Vernon Ave, Chestertown

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

Selling Office: Benson & Mangold, LLC.

201 Birch Run Rd, Chestertown
$430,000
3 Beds ⋅ 2 Baths
*****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Eastern Shore lifestyle. The Mile Tree Village community is tucked on a quiet cul-de-sac with views of the Chester River. The home has been thoughtfully improved with major 2021 updates including joist replacement, flooring, crawl space encapsulation, and rear fencing all performed by the greatest hits list of Kent County craftsmen, along with freshly stained rough-cut cedar siding in 2025. An oversized two-car garage, serene courtyard with water feature, and a spacious, partially shaded backyard with deck seating create a setting that feels both private and inviting—all just a short walk to downtown shops, restaurants, Washington College, and the town’s parks.

201 Birch Run Rd, Chestertown

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

Selling Office: Blackwell Real Estate, LLC.

21007 Bayside Ave, Rock Hall
$425,000
3 Beds ⋅ 2 Baths
Adorable updated cottage in the heart of town on popular Bayside Avenue offering approximately 1,400 sq. ft. of charming coastal living. This delightful Cape Cod features 3 bedrooms and 2 full baths, with seasonal water views of Rock Hall Harbor from the second floor. The main level offers an open floor plan with a cozy propane fireplace, 2 bedrooms, and 1 full bath, while the entire upper level serves as a spacious private primary suite. Enjoy outdoor living in the fenced rear yard — perfect for pets, entertaining, or relaxing on the back deck while taking in the scenery. A detached one-car garage and storage shed provide plenty of room for bikes, tools, kayaks, and LSV/golf cart storage. Ideally located within walking distance to local favorites including Harbor Shack and Waterman’s Crab House, marinas, harbor festivities, shops, and more. Conveniently situated along the complimentary Rock Hall Rides shuttle route, making it easy to enjoy everything this waterfront town has to offer!

21007 Bayside Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

21120 Green Ln, Rock Hall
$419,000
3 Beds ⋅ 2 Baths
COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax, entertain, and enjoy the Eastern Shore lifestyle. The spacious detached garage provides ample storage for vehicles, boats, and recreational equipment. Unwind in the cooled three-season room overlooking the fenced backyard, offering the perfect setting for gatherings with family and friends after a day on the water. Ideally located just a short walk or golf cart ride from Haven Harbour South Marina, you'll enjoy convenient access to boat slips, waterfront dining, a sandy beach, marina amenities, and breathtaking Chesapeake Bay sunsets. Whether you're seeking a year-round residence, weekend escape, or boating retreat, this property offers comfort, convenience, and the best of Rock Hall living. Wake up, walk to your boat, spend the day on the Chesapeake Bay, enjoy waterfront dining, watch the sunset, and return home to relax in your private backyard. Every day feels like you're on vacation.

21120 Green Ln, Rock Hall

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

Selling Office: Real Broker, LLC - Annapolis.

12089 Blacks Station Rd, Kennedyville
$415,000
4 Beds ⋅ 2 Baths
Charming Cape Cod nestled on a beautiful 2-acre lot offering the perfect blend of space, privacy, and timeless charm! This well-maintained home features a long driveway, 2-car garage, and lovely landscaping that creates wonderful curb appeal. Inside, you’ll find hardwood floors on the main level along with fresh neutral paint throughout the home. The spacious sunroom addition is filled with natural light and offers peaceful views of the picturesque backyard. Nature lovers and gardeners will appreciate the mature fruit trees including apple, pear, and cherry, along with thriving raspberry, blueberry, and blackberry bushes. The flexible main-level bedroom with full bath is ideal for guests, a home office, or convenient one-level living. Upstairs offers generously sized bedrooms with plenty of space and character. Major updates have already been taken care of with a recently updated roof, HVAC system, water softener, and hot water heater. A rare opportunity to enjoy peaceful outdoor living with room to grow! 10 miles to 301, 20 minutes to Chestertown and Middletown.

12089 Blacks Station Rd, Kennedyville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Doug Ashley Realtors, LLC.

no property photo
$415,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 1.5-bath rancher offering 1,344 sq ft of comfortable, energy-efficient living. Thoughtfully improved since 2018, this home blends modern upgrades with inviting indoor and outdoor spaces. Step inside to find newer laminate flooring, updated baseboards, and a fully remodeled kitchen featuring soft-close cabinetry, butcher block countertops, and stainless steel appliances. The spacious sunroom is a true highlight, complete with new insulation, drywall, a charming shiplap ceiling, and a cozy gas fireplace with blower—perfect for year-round enjoyment. Major system upgrades provide peace of mind, including all new Pella energy-efficient windows (with six additional windows added to the family room), a 2022 architectural roof with ridge vents, new vinyl siding with added insulation and house wrap, and a fully encapsulated and insulated crawlspace with treated floor joists. The home is equipped with a high-efficiency 2-unit, 4-zone mini-split system (23 SEER), a tankless electric water heater, whole-house water filtration, and a 200-amp electrical panel with generator transfer switch. Enjoy seamless indoor-outdoor living with a 15’ x 19’ three-season sunroom featuring floor-to-ceiling E-Z Breeze windows, LVP flooring, and a ceiling fan. Outside, the 150’ x 100’ lot backs to trees for added privacy and includes a paver patio with firepit, retractable awning, and beautifully landscaped grounds. The fenced backyard features wood slat fencing with wire mesh, along with apple and fig trees, grapevines, greenhouse framing and raised beds for garden enthusiasts. Additional features include a new laundry room with half bath, updated main bath, new exterior doors with storm doors, upgraded lighting, gravel driveway, and a storage shed with added screened porch, power, and lighting (shed conveys as-is). Located on a quiet street, yet conveniently walkable to local restaurants and the beach, this move-in ready home offers the perfect blend of comfort, efficiency, and lifestyle.

20812 Mercer Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

411 Greenwood Ave, Chestertown
$415,000
3 Beds ⋅ 3 Baths
Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in closet and an en-suite bath which now boasts a soaking tub. Step outside to enjoy the large deck, fire pit patio, and fully fenced backyard. This home offers comfort and convenience at every turn. Just a few blocks from Washington College and a short stroll to Downtown Chestertown’s charming restaurants, shops, and waterfront.

411 Greenwood Ave, Chestertown

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

Selling Office: Monument Sotheby's International Realty.

6270 Rock Hall Rd, Rock Hall
$412,000
This 3,000 SF commercial building was originally constructed in 2001, but was significantly improved in 2020 and most recently used as a veterinary hospital. A 29 ft x 16 ft reception area, 8 treatment rooms/offices and 2 restrooms offer a user-owner or investor a flexible layout for a variety of uses. Dual heat pumps with propane back up provide multi-zoned conditioning for the building. Two ADA compliant bathrooms and an entry ramp are in place. There are sealed concrete floors in the work spaces and new high quality vinyl planked flooring in pubic areas. A 5KW Generac back up generator insures uninterrupted power to the building. The property is served by public water and sewer and there is a whole-building water filter installed. Crossroads Commercial zoning offers a wide range of permitted uses. Conveniently located on Rt. 20, 5 minutes outside the town of Rock Hall.

6270 Rock Hall Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

109 S College Ave, Chestertown
$410,000
3 Beds ⋅ 3 Baths
Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, you’ll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem

109 S College Ave, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: LPT Realty, LLC.

How much is your home worth?

Get instant property value now!